Country：Japan

Country：Japan

Country：Japan

Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jacs.0c03097

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/c8cc06543h

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.orglett.8b01480

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Nature Publishing Group  

Direct functionalization of amino groups in complex organic molecules is one of the most important key technologies in modern organic synthesis, especially in the synthesis of bio-Active chemicals and pharmaceuticals. Whereas numerous chemical reactions of amines have been developed to date, a selective, practical method for functionalizing complex amines is still highly demanded. Here we report the first late-stage N-Alkylation of pharmaceutically relevant amines with alcohols at ambient temperature. This reaction was achieved by devising a mixed heterogeneous photocatalyst in situ prepared from Cu/TiO2 and Au/TiO2. The mixed photocatalytic system enabled the rapid N-Alkylation of pharmaceutically relevant molecules, the selective mono-and di-Alkylation of primary amines, and the non-symmetrical dialkylation of primary amines to hetero-substituted tertiary amines.

DOI： 10.1038/s41598-018-25293-z

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Scopus

PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Walter de Gruyter GmbH  

A brief account of our recent work on the chemo-, regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to alkenes promoted by palladium-loaded titanium oxide (Pd/TiO2) photocatalysts is presented. Since methanol is employed as the reducing agent, the method does not involve stoichiometric generation of salt waste. The photocatalytic hydrogenolysis proceeds at room temperature, and is compatible with the presence of functional groups such as C=C double bonds and hydroxyl groups at non-allylic positions. The regioselectivity is predictable: the hydrogen atom is predominantly incorporated into the sterically less hindered carbon atom of the allylic moiety. This protocol should provide straightforward green access to a range of platform chemicals (exemplified by the two-step synthesis of propylene from glycerol) and fine chemicals [e.g. (S)-(+)-lavandulol from (R)-(-)-carvone] without the need for protection/deprotection steps.

DOI： 10.1515/pac-2017-0501

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Scopus

Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Carboxylic acids (CAs) are one of the most ubiquitous and important chemical feedstocks available from biorenewable resources, CO2, and the petrochemical industry. Unfortunately, chemoselective catalytic transformations of CHnCO2H (n = 1-3) groups into other functionalities remain a significant challenge. Herein, we report rhenium(V) complexes as extremely effective precatalysts for this purpose. Compared to previously reported heterogeneous and homogeneous catalysts derived from high- or low-valent metals, the present method involves a alpha-C-H bond functionalization, a hydrogenation, and a hydrogenolysis, which affords functionalized alcohols with a wide substrate scope and high chemoselectivity under relatively mild reaction conditions. The results represent an important step toward a paradigm shift from 'low-valent' to 'high-valent' metal complexes by exploring a new portfolio of selective functional group transformations of highly oxygenated organic substrates, as well as toward the exploitation of CAs as a valuable biorenewable feedstock.

DOI： 10.1038/s41598-017-03436-y

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Amides are ubiquitous and abundant in nature and our society, but are very stable and reluctant to salt-free, catalytic chemical transformations. Through the activation of a "sterically confined bipyridineruthenium (Ru) framework (molecularly well-designed site to confine adsorbed H-2 in)" of a precatalyst, catalytic hydrogenation of formamides through polyamide is achieved under a wide range of reaction conditions. Both C=O bond and C-N bond cleavage of a lactam became also possible using a single precatalyst. That is, catalyst diversity is induced by activation and stepwise multiple hydrogenation of a single precatalyst when the conditions are varied. The versatile catalysts have different structures and different resting states for multifaceted amide hydrogenation, but the common structure produced upon reaction with H-2, which catalyzes hydrogenation, seems to be "H-Ru-N-H."

DOI： 10.1038/s41598-017-01645-z

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Dehydrogenation reaction of primary aliphatic alcohols to aldehydes and molecular hydrogen was achieved under UV-vis light irradiation in the presence of gold-loaded titanium dioxide (Au/TiO2) photocatalysts.

DOI： 10.1246/cl.161195

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Carboxylic acids are ubiquitous in bio-renewable and petrochemical sources of carbon. Hydrogenation of carboxylic acids to yield alcohols produces water as the only byproduct, and thus represents a possible next generation, sustainable method for the production of these alternative energy carriers/platform chemicals on a large scale. Reported herein are molecular insights into cationic mononuclear ruthenium carboxylates ([Ru(OCOR)](+)) as prototypical catalysts for the hydrogenation of carboxylic acids. The substrate-derived coordinated carboxylate was found to function initially as a proton acceptor for the heterolytic cleavage of dihydrogen, and subsequently also as an acceptor for the hydride from [Ru-H](+), which was generated in the first step (self-induced catalysis). The hydrogenation proceeded selectively and at high levels of functional group tolerance, a feature that is challenging to achieve with existing heterogeneous/homogeneous catalyst systems. These fundamental insights are expected to significantly benefit the future development of metal carboxylate-catalysed hydrogenation processes of bio-renewable resources.

DOI： 10.1038/ncomms9140

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A novel method to prepare microstructured polymer brushes using TiO2 nanoparticles and photocatalytic microcontact printing is described. It is shown that ethanol amine can be polymerized to linear polyethyleneimine (PEI) driven by the photocatalytic action of TiO2. Upon UV irradiation during microcontact printing of ethanol amine with a stamp coated with TiO2 nanoparticles, patterned polymer brushes with a length of around 50 nm are obtained.

DOI： 10.1039/c4cc08646e

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Herein, catalytic fluoride (F-) is demonstrated to be a trigger for dehydrative immobilization of atmospheric pressure CO2, such that reaction of CO2 with beta-amino alcohols derived from natural amino acids gives optically pure oxazolidinones in high yields. A synergistic combination of fluoride and organosilicon agents (e.g., Bu4NF + Ph3SiF or siloxanes) enhances the catalytic activity and functional group compatibility. This system lies at the interface between homogenous and heterogeneous catalysis, and may prove useful for the development of recoverable/reusable siloxane-based CO2 immobilization materials.

DOI： 10.1039/c4ra09609f

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Dehydrative synthesis of oxazolidinones from amino alcohols and CO2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process. (C) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.06.100

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst. (c) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.03.047

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We have developed a new method for the direct aldol condensation of unactivated amides using 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)-based phosphorous/SO42- catalysis. The SO42- species in a reaction mixture enhances the reaction rate of the catalysis. In principle, no metal sources are required for the generation of the catalyst, and there is no requirement for the use of stoichiometric quantities of an acid or base. This catalyst system is operative under relatively acidic conditions. One major advantage of carrying out the reaction under acidic conditions is that both aldehydes and acetals are capable of undergoing carbon-carbon bond formation at the alpha-carbon of amide carbonyl groups through dehydration. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.07.129

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/chem.201101752

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.201006660

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H(2) gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high alcohol product selectivity.

DOI： 10.1039/b914618k

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

We have disclosed the catalytic potential hidden behind a series of aqua-aminoorganoboron compounds in the formation and reaction of nitronate species. The pivotal role of a single-coordinated water molecule in the catalyst was demonstrated by comparison with the D2O-analogue. The present results provide a new strategy for the design of metal-free catalysts which function via elaborative hydrogen-bonding networks involving water.

DOI： 10.1246/cl.2008.1294

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Proper design of acid-base catalysis has been shown to be effective for achieving high reactivity and selectivity in the asymmetric direct aldol reaction during the development of diamine-Bronsted acid types of catalyst. In this study, two principal approaches have been implemented to create a new type of catalysis and high catalytic efficiency: one is the creation of a highly viable acidic function within acid-base catalysts; the other is the creation of rather complicated but more cooperatively arranged hydrogen-bond networks that would be expected to stabilize a transition state, thereby promoting new reactivity and selectivity.

DOI： 10.1021/ar030064p

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Diastereoselective vinylogous direct aldol reaction was realized by use of chiral alpha,beta-unsaturated esters and aldehydes in the presence of aluminum tris[2,6-bis(4-alkylphenyl)phenoxide]s. The reaction involves novel 1,7-asymmetric induction and direct coupling of an alpha,beta-unsaturated ester with an aldehyde, through in situ deprotonation of the gamma-proton of the ester component by LTMP.

DOI： 10.1055/s-2004-817761

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.200352724

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.200352809

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A new method for the preparation of aluminum and titanium trisphenoxides was realized using tetraallyltin or alpha-pinene as a proton-trapping agent. Thus obtained chlorotitanium reagent was converted to the corresponding cation-type reagent, which proved to be an effective catalyst for epoxide rearrangements.

DOI： 10.1246/cl.2003.1006

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Various alpha,beta-unsaturated carbonyl compounds were coordinated with aluminum tris(2,6-diphenylphenoxide) (ATPH) to give the corresponding Lewis acid-base complexes in a distinctive coordination fashion (selective coordination). ATPH recognizes carbonyl substrates and subsequently orients itself as it forms a stable complex through selective coordination with the carbonyl oxygen. Selective coordination also confers a conformational preference to each carbonyl compound under the steric and electronic influence of ATPH, which enables the vinylogous aldol reaction of alpha,beta-unsaturated carbonyl compounds to give the corresponding gamma-aldol products with different regio- and stereoselectivities.

DOI： 10.1021/ja0205941

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The asymmetric coupling of various phenol or aniline derivatives with bulky aryllead triacetates was thoroughly investigated using optically active amines, including strychnine and brucine. We found that conformationally restricted tertiary amines, as well as lithium aryloxides and molecular sieves, are essential for accelerating the rate of phenol coupling. Consequently, the reaction can be carried out at a low temperature (-40 to -20 degreesC) and gives a high degree of diastereo- and enantioselectivity. In contrast to the effectiveness of lithiation in phenol coupling, magnesation of anilines was a critical technique for aniline coupling with aryllead triacetates. Using these coupling methods, a diverse set of di-, tri, and polyaryl compounds with axial chirality can be easily obtained, and these should be useful for the construction of a variety of aryl-aryl frameworks involved in metal ligands, natural products, and artificial helical polymers.

DOI： 10.1021/ja012287l

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/S0040-4020(00)01042-5

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja0014382

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja000789d

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ja990646v

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1351/pac199971020239

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ja972765l

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/(SICI)1521-3773(19981231)37:24<3378::AID-ANIE3378>3.0.CO;2-L

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/a607464b

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/jo970747g

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/a702684f

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/a-2124-4037

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.inorgchem.3c02412

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/ajoc.202300230

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.ccr.2022.214773

Authorship：Last author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.2c05034

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

A novel mononuclear ruthenium (Ru) complex bearing a PNNP-type tetradentate ligand is introduced here as a self-photosensitized catalyst for the reduction of carbon dioxide (CO2). When the pre-activation of the Ru complex by reaction with a base was carried out, an induction period of catalyst almost disappeared and the catalyst turnover numbers (TONs) over a reaction time of 144 h reached 307 and 489 for carbon monoxide (CO) and for formic acid (HCO2H), respectively. The complex has a long lifespan as a dual photosensitizer and reduction catalyst, due to the sterically bulky and structurally robust (PNNP)Ru framework. Isotope labeling experiments under 13CO2 atmosphere indicate that CO and HCO2H were both produced from CO2.

DOI： 10.1055/a-1709-0280

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/d2cc01701f

Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.organomet.2c00171

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.joc.1c02318

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PubMed

Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/a-1577-5947

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/d1ra00988e

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

<p>The redox-neutral addition of α-C–H bonds to styrenes was enabled via the hydrogen-atom transfer to aqueous hydroxyl radical generated by the oxidation of water under silver-nanoparticle-loaded titania photocatalysis.</p>

DOI： 10.1039/d1gc00753j

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20210023

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using 31P NMR spectroscopy and ESI mass spectrometry.

DOI： 10.1055/s-0040-1707174

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

DOI： 10.5059/yukigoseikyokaishi.78.856

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/adsc.201901298

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201901298

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.orglett.8b03271

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acssuschemeng.8b03855

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(-)-carvone by avoiding otherwise necessary protection/deprotection steps.

DOI： 10.1002/chem.201704099

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

N-Allylamines were employed for the diastereoselective synthesis of 8-bromo-substituted, cis-configured perhydroquinoxalines and beta-bromoalcohols. The yield and constitution of the products depend considerably on the functionalization of the allylic N-atom. Herein the reaction of glycine-derived cyclohex-2-enamines 5 under bromolactamization conditions (LiOtBu, NBS) is reported. Methyl carbamate 5a led diastereoselectively to the cis-configured perhydroquinoxaline 6a, whereas the amides 5b and 5c provided cis, trans-configured -bromoalcohols 7b and 7c. Based on high level theoretical calculations (DFT) factors controlling the cyclization of lithiated intermediates and the relative energies of possible products are discussed.

DOI： 10.1002/jhet.2493

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

The ruthenium (Ru) precatalyst complex dichlorobis[2-[(dicyclohexylphosphino-kappa P)methyl]pyridine- kappa N]ruthenium(II) (RuPCY), first developed by us, was shown to be useful not only for the catalytic hydrogenation of inert carboxylic acid derivatives including amides and esters, but also for the catalytic dehydrogenation of primary (1 degrees) and secondary (2 degrees) alcohols and subsequent reactions. RuPCY is versatile, and different Ru catalysts derived therefrom are quite useful for realizing a variety of indiscrete/discrete catalytic hydrogen management (HyMA) reactions. The sequential use of different starting materials and different catalysts (all derived from RuPCY) permits otherwise challenging orthogonal HyMA processes. This accommodates, for example, a salt-free access and/or shortcut to synthetic intermediates of pharmaceutically important substances such as donepezil (Aricept (R)) and atorvastatin (Lipitor (R)).

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

The morphan system (2-azabicyclo[3.3.1]no-nane) as a substructure of morphine is of major interest in medicinal chemistry. Herein, the synthesis of morphan derivatives with additional substituents at the propano bridge is reported. In order to avoid the isolation of the smelly and volatile nitrile 6 and the very polar primary amine 9, an efficient one-pot, three-step sequential transformation of the mesylate 5 into amides 10 was developed. The key step of the synthesis was the stereoselective intramolecular opening of the epoxides 11a-d leading to the exo-configured 8-hydroxymorphans 12a-d. The configuration of the exo-configured hydroxymorphan 12d bearing the kappa- and sigma-pharmacophoric 3,4-dichlorophenylacetyl moiety was inverted by oxidation and stereoselective reduction. An X-ray crystal structure analysis of the benzamide 12c confirmed the relative configuration of the hydroxymorphans 12a-d and 14d.

DOI： 10.1515/znb-2016-0129

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

cis,cis-Configured perhydroquinoxaline-5-carbonitrile 10 was synthesized stereoselectively by ditosylation of trans,cis-2,3-dihydroxycyclohexane-1-carbonitrile 4 and subsequent reaction with ethylenediamine. The diol precursor 4 was stereoselectively obtained by regioselective opening of the epoxide 3 with KCN in water avoiding hazardous Et2AlCN.

DOI： 10.1002/jhet.2322

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups.

DOI： 10.1021/acs.orglett.5b01063

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/c4ra15682j

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Compounds based on the pyrroloquinoxaline system can interact with serotonin 5-HT3, cannabinoid CB1, and -opioid receptors. Herein, a chiral pool synthesis of diastereomerically and enantiomerically pure bromolactam (S,R,R,R)-14A is presented. Introduction of the cyclohexenyl ring at the N-atom of (S)-proline derivatives 8 or methyl (S)-pyroglutamate (12) led to the N-cyclohexenyl substituted pyrrolidine derivatives 4 and 13, respectively. All attempts to cyclize the (S)-proline derivatives 4 with a basic pyrrolidine N-atom via [3+2] cycloaddition, aziridination, or bromolactamization failed. Fast aromatization occurred during treatment of cyclohexenamines under halolactamization conditions. In contrast, reaction of a 1:1 mixture of diastereomeric pyroglutamates (S,R)-13bA and (S,S)-13bB with (LiOBu)-Bu-t and NBS provided the tricyclic bromolactam (S,R,R,R)-14A with high diastereoselectivity from (S,R)-13bA, but did not transform the diastereomer (S,S)-13bB. The different behavior of the diastereomeric pyroglutamates (S,R)-13bA and (S,S)-13bB is explained by different energetically favored conformations. Chirality 26:793-800, 2014. (c) 2014 Wiley Periodicals, Inc.

DOI： 10.1002/chir.22350

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

The first stereoselective synthesis of a cis, cis-configured vicinal triamine was achieved, starting from N-cyclohexenylpyrrolidone (10). The reaction sequence consists of the stereoselective construction of the trans-configured 1,3-diamide 14, trans-to-cis isomerization via enols or enamines, and subsequent highly stereoselective reduction of the intermediate imine 17D to the amine 18A. The postulated reaction pathway explains the observed stereoconvergence and is supported by calculation of the heats of formation of its intermediates at the PM3 level. LiAlH4 reduction of 18A yielded the tetracyclic aminal 19, which was converted into the pyrrolidinylquinoxaline 7, which showed low to moderate affinity towards. and sigma(1) receptors.

DOI： 10.1002/ejoc.201402685

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/c4cy00329b

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

A virtually salt-free and straightforward bimolecular assembly giving N-unsubstituted pyrroles through fully unmasked a-amino aldehydes, which was enabled by the dual effects of a catalytic ruthenium complex and an alkali metal base, is reported. Either solvent-free or acceptorless dehydrogenation facilitates high atom, step, and pot economy, which are otherwise difficult to achieve in multistep operations involving protection/deprotection.

DOI： 10.1021/ol4001262

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

D-(+)-Camphor forms the enamine 2 with piperidine. Compound 2 adds HB(C6F5)(2) at the enamine carbon atom C3 to form a Lewis acid/Lewis base adduct (exo-/endo-isomers of 3). Exposure of 3 to dihydrogen (2.5 bar, room temperature) leads to heterolytic splitting of H-2 to form the H+/H- addition products (4, two diastereoisomers) of the "invisible" frustrated Lewis pairs (5, two diastereoisomers) that were apparently generated in situ by enamine hydroboration under equilibrium conditions.

DOI： 10.1002/asia.201200776

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Carbon dioxide is immobilized into dialkyl carbonate using acetals of N,N-dimethylformamide under atmospheric pressure. No special treatment with tailor-made catalysts is needed. Use of dimethyl sulfoxide as a solvent is critical. An ambiphilic mechanism is proposed for the direct synthesis of dialkyl carbonates from acetals and carbon dioxide. © 2013 The Chemical Society of Japan.

DOI： 10.1246/cl.2013.146

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Scopus

Authorship：Lead author   Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.201200304

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/chem.201102446

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

DOI： 10.1002/asia.201000921

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PubMed

Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We introduced here a new one-pot, general procedure for the preparation of dialkyl carbonates from alcohols in a straightforward fashion under 1 atm pressure of CO2 using Cs2CO3 and CH2Cl2 as key reagents. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2010.10.051

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

A proline-derived silanol, was designed as a novel potential organocatalyst, and synthesized starting from the tetrazole 3. The central idea was the combination of all acidic (tetrazole) and a basic functionality (pyrrolidine) with a silanol moiety in the same molecule. The synthesis of 7 was performed ill four reaction steps starting with the tetrazole 3. In the solid state (X-ray crystal Structure analysis) the crucial functional groups show a favorable orientation. A chiral HPLC method and a chiral capillary electrophoresis method have been established for the investigation of the kinetic resolution of the racemic alcohols 9 and 11. Acetylation reactions of alcohols were not accelerated by the organocatalyst 7, and the produced ee values were rather low.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

We disclosed structural dynamics hidden behind a series of aminoorganoboron (AOB) compounds that involved a recombinant of covalent, dative, and hydrogen bonds. A combination process occurred via reorganizing elements and bonds between the two major structures (open and closed), which were chemically switchable through precise adjustment of either acidic or basic conditions. The structural dynamics favoring an open structure seem to be more important for catalysis, as represented by methanolysis of activated amides.

DOI： 10.1021/ja9029494

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CSIRO PUBLISHING  

1,4-Diazabicyclo[3.3.1] nonanes (aza-morphans) represent conformationally constrained piperazine derivatives. Herein, we report a six-step synthesis of the benzyl and allyl substituted bicyclic ketones 3a and 3b, which represent interesting building blocks for the synthesis of conformationally restricted receptor ligands. The key steps of the synthesis are the regioselective addition of ethyl acrylate to the piperazine 8, the sodium hexamethyldisilazide-induced Dieckmann cyclization of the diesters 10, and the decarboxylation of the enol esters 11 with dilute HCl. The complete sequence is only successful when a benzyl (10a) or allyl moiety (10b) is attached to N-1, since the tosyl derivative 10f failed to give a Dieckmann cyclization product, and the decarboxylation failed with the acyl derivatives 11c and 11d.

DOI： 10.1071/CH09206

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

Proper design of amine-Bronsted acid catalysis has been shown to be effective for achieving high reactivity and selectivity in the asymmetric direct aldol reaction. During the course of this study, two principal approaches have been implemented to create a new type of catalysis: One is derived from Bronsted acid and diamine; the other is pyrrolidine with tetrazole functionality. The developed amine-Bronsted acid catalysts have been found to effectively catalyze the direct aldol reaction of aldehyde, chloral and nitrosobenzene.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

An aldol-type reaction of organonitriles with aldehydes was catalyzed by a Rh(I)(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components.

DOI： 10.1039/b800634b

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Language：English   Publishing type：Research paper (scientific journal)  

Authorship：Lead author   Language：Japanese  

Authorship：Lead author   Language：Japanese  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Authorship：Lead author   Language：Japanese  

Authorship：Lead author   Language：Japanese  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：NATL ACAD SCIENCES  

The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Bronsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.

DOI： 10.1073/pnas.0307785101

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PubMed

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Fifteen different diamines (4-18) and potonic acids have been screened in the catalytic asymmetric direct aldol reaction of three different aldehydes in acetone. These initial studies demonstrated that the secondary-tertiary diamine series is effective with regard to reactivity. In contrast, the primary-tertiary diamines 13 and 14 were proved to be a superb structural module to avoid dehydration. Further investigation led us to a new procedure for the preparation of diamine catalysts for synthetic convenience. This involves diamine-diacid salt 22, which acted not only as a catalyst backbone but also as a TfOH source. Salt 22-diamine 4 catalyst thus prepared was found to exhibit higher reactivity and selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

The 1,2-addition of organomagnesium reagents to p-methoxyphenyl(PMP)amine-derived aldimines proceeded effectively in the presence of catalytic amounts of Sc(OTf)(3).

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Four different protonic acids and 15 diamines were screened in the catalytic asymmetric direct aldol reaction of three different aldehydes in acetone.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of ortho-alkoxy (or ortho-fluoro) aniline-derived aldimines which found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate, which has optically pure 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as a chiral auxiliary with axial chirality. A Lewis acid additive is likely to have a complementary role in the pronounced activation of imine functionalities in the Mannich-type addition of the bulky chiral acetate. (C) 2001 Elsevier Science Ltd. All rights reserved.

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Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

A one-pot three-component coupling involving organolithium reagents, ATPH·cyclopentenone complex, and dihydrofuran·BCl3 complex (see scheme) gives moderate to good yields of the products with selective formation of either the 2,3-cis or 2,3-trans isomer, depending on the nature of the lithium reagent.

DOI： 10.1002/1521-3773(20011001)40:19<3613::AID-ANIE3613>3.0.CO;2-3

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Scopus

PubMed

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

The aryl-aryl coupling of aryllead triacetates at the ortho-position of anilines was achieved by simple magnesation of the aniline nitrogen.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A regio- and enantioselective siloxybutylation at the more hindered alpha-site of unsymmetrical dialkyl ketones was achieved to give a quarternary carbon center by the combined use of the chiral aluminum trisnaphthoxide (R)-ATBN and a base.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of o-alkoxy (or o-fluoro) aniline-derived aldimines which have been found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate. A Lewis acid additive has a complementary role in the pronounced activation of imine functionalities.

DOI： 10.1021/ol000099e

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PubMed

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Authorship：Lead author   Language：Japanese  

Language：English   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

The present article covers the progress in directed aldol condensation, which can be divided into three different classes. First, the mixed aldol condensation that uses general acids or bases under protic conditions. Second, stepwise enolization-aldolization sequence that utilizes various metal enolates under aprotic conditions. Third, a novel mixed aldol condensation that makes use of a bulky Lewis acid and a lithium amide under aprotic conditions. The scope and limitation of each of three aldol strategies is discussed.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A ketone, cyclic ether, and epoxide are combined in one-pot using aluminum tris(2,6-diphenylphenoxide) (ATPH) and LDA, the latter agent being applied as the trigger for the reaction.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

The present paper covers the progress in stereo-, regio-, and chemoselective carbon-carbon bond-forming reactions promoted by structurally well-designed aluminum aryloxides. Compared with conventional Lewis acids, these aluminum reagents strongly coordinate with various oxygen-containing substrates, and the coordination aptitude is strongly affected by the steric environment of the metal ligands. In principle, the carbonyl groups of the bound substrates are electronically activated but sterically deactivated depending on the aluminum reagent and the type of the reaction employed. This review specifically highlights the selective organic reactions using ATPH.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A newly introduced, solid polymer of an aluminum trisphenoxide has been demonstrated an efficient catalyst for promoting the Diels-Alder reaction of alpha,beta-enals.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG  

Various lithium enolates of esters undergo effective 1,6-addition to aromatic carbonyl compounds in the presence of aluminum tris(2,6-diphenylphenoxide)(ATPH).

Web of Science

Language：English   Publishing type：Research paper (scientific journal)  

The combined use of aluminum tris(2,6-diphenylphenoxide) (ATPH) and lithium 2,2,6,6-tetramethylpiperidide (LTMP) has proven to be effective for the mixed crossed aldol condensation between conjugated esters and various aldehydes. An example is shown in Equation (1).

DOI： 10.1002/(SICI)1521-3773(19990614)38:12<1769::AID-ANIE1769>3.0.CO;2-0

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Scopus

PubMed

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

A variety of Lewis acid reagents were utilized for Diels-Alder, aldol, and ene reactions with high enantioselectivities. The origin of the selectivity of these reactions is discussed.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Sterically hindered aluminium aryloxides have been developed as designer Lewis acid catalysts for stereo-, regio- and chemo-selective carbon-carbon bond-forming reactions. Compared with classical Lewis acids, these aluminium reagents coordinate strongly with various oxygen-containing substrates, and this coordination is affected by the steric environment of their ligands, The carbonyl groups of the bound substrates are either electronically activated or sterically deactivated depending on the aluminium reagent used and the type of reaction, Designer chiral catalysts based on the structure of these bulky aluminium reagents have also been examined.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Conjugate 1,6-addition of silyllithium reagents to aromatic carbonyl substrates in the presence of the carbonyl protector aluminium tris(2,6-diphenylphenoxide) (ATPH) gives allylsilanes.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Michael addition of lithium enolates derived from ketones to a variety of alpha, beta-unsaturated ketones was realized in the presence of aluminum tris(2,6-diphenylphenoxide) (ATPH). In this reaction, ATPH can be used as a carbonyl protector of alpha, beta-unsaturated carbonyl substrates upon complexation, which facilitates the regioselective 1,4-addition of lithium enolates to Michael accepters. Similarly, dianions of beta-dicarbonyl compounds undergo Michael addition smoothly using ATPH as an effective promoter of the reaction. Subsequent regioselective, intramolecular aldol condensation was also demonstrated, leading to bicyclic carbon ring systems. Such systems are difficult to obtain by the Robinson annulation usually performed in protic media.

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

An annulation system based on sequential inter- and intramolecular Michael addition was realized by the combined use of ketone enolates and aluminum tris(2,6-diphenylphenoxide)(ATPH).

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Various ketones can be alkylated with tetrahydrofuran (THF) to provide alpha-siloxybutylated ketones in the presence of a bulky aluminum reagent, lithium diisopropylamide (LDA), and t-butyldimethylsilyl triflate (TBSOTf).

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A new Lewis acidic receptor, aluminum tris(4-bromo-2,6-diphenylphenoxide)(ATPH-Br), is a powerful promoter of the Claisen rearrangement of various allyl vinyl ethers and is effective for controlling the stereochemistry of the resulting rearrangement products.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Amides are ubiquitous and abundant in nature and our society, but are very stable and reluctant to salt-free, catalytic chemical transformations. Through the activation of a "sterically confined bipyridineruthenium (Ru) framework (molecularly well-designed site to confine adsorbed H-2 in)" of a precatalyst, catalytic hydrogenation of formamides through polyamide is achieved under a wide range of reaction conditions. Both C=O bond and C-N bond cleavage of a lactam became also possible using a single precatalyst. That is, catalyst diversity is induced by activation and stepwise multiple hydrogenation of a single precatalyst when the conditions are varied. The versatile catalysts have different structures and different resting states for multifaceted amide hydrogenation, but the common structure produced upon reaction with H-2, which catalyzes hydrogenation, seems to be "H-Ru-N-H."

DOI： 10.1038/s41598-017-01645-z

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Dehydrogenation reaction of primary aliphatic alcohols to aldehydes and molecular hydrogen was achieved under UV-vis light irradiation in the presence of gold-loaded titanium dioxide (Au/TiO2) photocatalysts.

DOI： 10.1246/cl.161195

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)  

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)  

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-BLACKWELL  

N-Allylamines were employed for the diastereoselective synthesis of 8-bromo-substituted, cis-configured perhydroquinoxalines and beta-bromoalcohols. The yield and constitution of the products depend considerably on the functionalization of the allylic N-atom. Herein the reaction of glycine-derived cyclohex-2-enamines 5 under bromolactamization conditions (LiOtBu, NBS) is reported. Methyl carbamate 5a led diastereoselectively to the cis-configured perhydroquinoxaline 6a, whereas the amides 5b and 5c provided cis, trans-configured -bromoalcohols 7b and 7c. Based on high level theoretical calculations (DFT) factors controlling the cyclization of lithiated intermediates and the relative energies of possible products are discussed.

DOI： 10.1002/jhet.2493

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

The morphan system (2-azabicyclo[3.3.1]no-nane) as a substructure of morphine is of major interest in medicinal chemistry. Herein, the synthesis of morphan derivatives with additional substituents at the propano bridge is reported. In order to avoid the isolation of the smelly and volatile nitrile 6 and the very polar primary amine 9, an efficient one-pot, three-step sequential transformation of the mesylate 5 into amides 10 was developed. The key step of the synthesis was the stereoselective intramolecular opening of the epoxides 11a-d leading to the exo-configured 8-hydroxymorphans 12a-d. The configuration of the exo-configured hydroxymorphan 12d bearing the kappa- and sigma-pharmacophoric 3,4-dichlorophenylacetyl moiety was inverted by oxidation and stereoselective reduction. An X-ray crystal structure analysis of the benzamide 12c confirmed the relative configuration of the hydroxymorphans 12a-d and 14d.

DOI： 10.1515/znb-2016-0129

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-BLACKWELL  

cis,cis-Configured perhydroquinoxaline-5-carbonitrile 10 was synthesized stereoselectively by ditosylation of trans,cis-2,3-dihydroxycyclohexane-1-carbonitrile 4 and subsequent reaction with ethylenediamine. The diol precursor 4 was stereoselectively obtained by regioselective opening of the epoxide 3 with KCN in water avoiding hazardous Et2AlCN.

DOI： 10.1002/jhet.2322

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：NATURE PUBLISHING GROUP  

Carboxylic acids are ubiquitous in bio-renewable and petrochemical sources of carbon. Hydrogenation of carboxylic acids to yield alcohols produces water as the only byproduct, and thus represents a possible next generation, sustainable method for the production of these alternative energy carriers/platform chemicals on a large scale. Reported herein are molecular insights into cationic mononuclear ruthenium carboxylates ([Ru(OCOR)](+)) as prototypical catalysts for the hydrogenation of carboxylic acids. The substrate-derived coordinated carboxylate was found to function initially as a proton acceptor for the heterolytic cleavage of dihydrogen, and subsequently also as an acceptor for the hydride from [Ru-H](+), which was generated in the first step (self-induced catalysis). The hydrogenation proceeded selectively and at high levels of functional group tolerance, a feature that is challenging to achieve with existing heterogeneous/homogeneous catalyst systems. These fundamental insights are expected to significantly benefit the future development of metal carboxylate-catalysed hydrogenation processes of bio-renewable resources.

DOI： 10.1038/ncomms9140

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups.

DOI： 10.1021/acs.orglett.5b01063

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A novel method to prepare microstructured polymer brushes using TiO2 nanoparticles and photocatalytic microcontact printing is described. It is shown that ethanol amine can be polymerized to linear polyethyleneimine (PEI) driven by the photocatalytic action of TiO2. Upon UV irradiation during microcontact printing of ethanol amine with a stamp coated with TiO2 nanoparticles, patterned polymer brushes with a length of around 50 nm are obtained.

DOI： 10.1039/c4cc08646e

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-BLACKWELL  

Compounds based on the pyrroloquinoxaline system can interact with serotonin 5-HT3, cannabinoid CB1, and -opioid receptors. Herein, a chiral pool synthesis of diastereomerically and enantiomerically pure bromolactam (S,R,R,R)-14A is presented. Introduction of the cyclohexenyl ring at the N-atom of (S)-proline derivatives 8 or methyl (S)-pyroglutamate (12) led to the N-cyclohexenyl substituted pyrrolidine derivatives 4 and 13, respectively. All attempts to cyclize the (S)-proline derivatives 4 with a basic pyrrolidine N-atom via [3+2] cycloaddition, aziridination, or bromolactamization failed. Fast aromatization occurred during treatment of cyclohexenamines under halolactamization conditions. In contrast, reaction of a 1:1 mixture of diastereomeric pyroglutamates (S,R)-13bA and (S,S)-13bB with (LiOBu)-Bu-t and NBS provided the tricyclic bromolactam (S,R,R,R)-14A with high diastereoselectivity from (S,R)-13bA, but did not transform the diastereomer (S,S)-13bB. The different behavior of the diastereomeric pyroglutamates (S,R)-13bA and (S,S)-13bB is explained by different energetically favored conformations. Chirality 26:793-800, 2014. (c) 2014 Wiley Periodicals, Inc.

DOI： 10.1002/chir.22350

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Herein, catalytic fluoride (F-) is demonstrated to be a trigger for dehydrative immobilization of atmospheric pressure CO2, such that reaction of CO2 with beta-amino alcohols derived from natural amino acids gives optically pure oxazolidinones in high yields. A synergistic combination of fluoride and organosilicon agents (e.g., Bu4NF + Ph3SiF or siloxanes) enhances the catalytic activity and functional group compatibility. This system lies at the interface between homogenous and heterogeneous catalysis, and may prove useful for the development of recoverable/reusable siloxane-based CO2 immobilization materials.

DOI： 10.1039/c4ra09609f

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Dehydrative synthesis of oxazolidinones from amino alcohols and CO2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process. (C) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.06.100

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst. (c) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2013.03.047

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)  

Carbon dioxide is immobilized into dialkyl carbonate using acetals of N,N-dimethylformamide under atmospheric pressure. No special treatment with tailor-made catalysts is needed. Use of dimethyl sulfoxide as a solvent is critical. An ambiphilic mechanism is proposed for the direct synthesis of dialkyl carbonates from acetals and carbon dioxide. © 2013 The Chemical Society of Japan.

DOI： 10.1246/cl.2013.146

Scopus

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We have developed a new method for the direct aldol condensation of unactivated amides using 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)-based phosphorous/SO42- catalysis. The SO42- species in a reaction mixture enhances the reaction rate of the catalysis. In principle, no metal sources are required for the generation of the catalyst, and there is no requirement for the use of stoichiometric quantities of an acid or base. This catalyst system is operative under relatively acidic conditions. One major advantage of carrying out the reaction under acidic conditions is that both aldehydes and acetals are capable of undergoing carbon-carbon bond formation at the alpha-carbon of amide carbonyl groups through dehydration. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.07.129

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/chem.201101752

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Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-BLACKWELL  

DOI： 10.1002/asia.201000921

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H(2) gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high alcohol product selectivity.

DOI： 10.1039/b914618k

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

We have disclosed the catalytic potential hidden behind a series of aqua-aminoorganoboron compounds in the formation and reaction of nitronate species. The pivotal role of a single-coordinated water molecule in the catalyst was demonstrated by comparison with the D2O-analogue. The present results provide a new strategy for the design of metal-free catalysts which function via elaborative hydrogen-bonding networks involving water.

DOI： 10.1246/cl.2008.1294

Web of Science

Language：Japanese   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

Proper design of amine-Bronsted acid catalysis has been shown to be effective for achieving high reactivity and selectivity in the asymmetric direct aldol reaction. During the course of this study, two principal approaches have been implemented to create a new type of catalysis: One is derived from Bronsted acid and diamine; the other is pyrrolidine with tetrazole functionality. The developed amine-Bronsted acid catalysts have been found to effectively catalyze the direct aldol reaction of aldehyde, chloral and nitrosobenzene.

Web of Science

Language：English   Publishing type：Book review, literature introduction, etc.   Publisher：AMER CHEMICAL SOC  

Proper design of acid-base catalysis has been shown to be effective for achieving high reactivity and selectivity in the asymmetric direct aldol reaction during the development of diamine-Bronsted acid types of catalyst. In this study, two principal approaches have been implemented to create a new type of catalysis and high catalytic efficiency: one is the creation of a highly viable acidic function within acid-base catalysts; the other is the creation of rather complicated but more cooperatively arranged hydrogen-bond networks that would be expected to stabilize a transition state, thereby promoting new reactivity and selectivity.

DOI： 10.1021/ar030064p

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：NATL ACAD SCIENCES  

The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Bronsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.

DOI： 10.1073/pnas.0307785101

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Diastereoselective vinylogous direct aldol reaction was realized by use of chiral alpha,beta-unsaturated esters and aldehydes in the presence of aluminum tris[2,6-bis(4-alkylphenyl)phenoxide]s. The reaction involves novel 1,7-asymmetric induction and direct coupling of an alpha,beta-unsaturated ester with an aldehyde, through in situ deprotonation of the gamma-proton of the ester component by LTMP.

DOI： 10.1055/s-2004-817761

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.200352724

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/anie.200352809

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A new method for the preparation of aluminum and titanium trisphenoxides was realized using tetraallyltin or alpha-pinene as a proton-trapping agent. Thus obtained chlorotitanium reagent was converted to the corresponding cation-type reagent, which proved to be an effective catalyst for epoxide rearrangements.

DOI： 10.1246/cl.2003.1006

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

Various alpha,beta-unsaturated carbonyl compounds were coordinated with aluminum tris(2,6-diphenylphenoxide) (ATPH) to give the corresponding Lewis acid-base complexes in a distinctive coordination fashion (selective coordination). ATPH recognizes carbonyl substrates and subsequently orients itself as it forms a stable complex through selective coordination with the carbonyl oxygen. Selective coordination also confers a conformational preference to each carbonyl compound under the steric and electronic influence of ATPH, which enables the vinylogous aldol reaction of alpha,beta-unsaturated carbonyl compounds to give the corresponding gamma-aldol products with different regio- and stereoselectivities.

DOI： 10.1021/ja0205941

Web of Science

Language：English   Publishing type：Book review, literature introduction, etc.   Publisher：AMER CHEMICAL SOC  

The asymmetric coupling of various phenol or aniline derivatives with bulky aryllead triacetates was thoroughly investigated using optically active amines, including strychnine and brucine. We found that conformationally restricted tertiary amines, as well as lithium aryloxides and molecular sieves, are essential for accelerating the rate of phenol coupling. Consequently, the reaction can be carried out at a low temperature (-40 to -20 degreesC) and gives a high degree of diastereo- and enantioselectivity. In contrast to the effectiveness of lithiation in phenol coupling, magnesation of anilines was a critical technique for aniline coupling with aryllead triacetates. Using these coupling methods, a diverse set of di-, tri, and polyaryl compounds with axial chirality can be easily obtained, and these should be useful for the construction of a variety of aryl-aryl frameworks involved in metal ligands, natural products, and artificial helical polymers.

DOI： 10.1021/ja012287l

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

The 1,2-addition of organomagnesium reagents to p-methoxyphenyl(PMP)amine-derived aldimines proceeded effectively in the presence of catalytic amounts of Sc(OTf)(3).

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Four different protonic acids and 15 diamines were screened in the catalytic asymmetric direct aldol reaction of three different aldehydes in acetone.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of ortho-alkoxy (or ortho-fluoro) aniline-derived aldimines which found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate, which has optically pure 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as a chiral auxiliary with axial chirality. A Lewis acid additive is likely to have a complementary role in the pronounced activation of imine functionalities in the Mannich-type addition of the bulky chiral acetate. (C) 2001 Elsevier Science Ltd. All rights reserved.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

The aryl-aryl coupling of aryllead triacetates at the ortho-position of anilines was achieved by simple magnesation of the aniline nitrogen.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja0014382

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/ja000789d

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of o-alkoxy (or o-fluoro) aniline-derived aldimines which have been found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate. A Lewis acid additive has a complementary role in the pronounced activation of imine functionalities.

DOI： 10.1021/ol000099e

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A ketone, cyclic ether, and epoxide are combined in one-pot using aluminum tris(2,6-diphenylphenoxide) (ATPH) and LDA, the latter agent being applied as the trigger for the reaction.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

The present paper covers the progress in stereo-, regio-, and chemoselective carbon-carbon bond-forming reactions promoted by structurally well-designed aluminum aryloxides. Compared with conventional Lewis acids, these aluminum reagents strongly coordinate with various oxygen-containing substrates, and the coordination aptitude is strongly affected by the steric environment of the metal ligands. In principle, the carbonyl groups of the bound substrates are electronically activated but sterically deactivated depending on the aluminum reagent and the type of the reaction employed. This review specifically highlights the selective organic reactions using ATPH.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A newly introduced, solid polymer of an aluminum trisphenoxide has been demonstrated an efficient catalyst for promoting the Diels-Alder reaction of alpha,beta-enals.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG  

Various lithium enolates of esters undergo effective 1,6-addition to aromatic carbonyl compounds in the presence of aluminum tris(2,6-diphenylphenoxide)(ATPH).

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WALTER DE GRUYTER GMBH  

A variety of Lewis acid reagents were utilized for Diels-Alder, aldol, and ene reactions with high enantioselectivities. The origin of the selectivity of these reactions is discussed.

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

An annulation system based on sequential inter- and intramolecular Michael addition was realized by the combined use of ketone enolates and aluminum tris(2,6-diphenylphenoxide)(ATPH).

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Language：English   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)   Publisher：AMER CHEMICAL SOC  

Web of Science

Event date： 2024.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス，船橋   Country：Japan  

Event date： 2024.3

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：日本大学理工学部船橋キャンパス，船橋   Country：Japan  

Event date： 2024.3

Language：Japanese   Presentation type：Poster presentation  

Venue：日本大学理工学部船橋キャンパス，船橋   Country：Japan  

Event date： 2024.3

Language：Japanese   Presentation type：Poster presentation  

Venue：日本大学理工学部船橋キャンパス，船橋   Country：Japan  

Event date： 2024.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス，船橋   Country：Japan  

Event date： 2024.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：日本大学理工学部船橋キャンパス，船橋   Country：Japan  

Event date： 2024.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋大学野依記念物質科学研究館   Country：Japan  

Event date： 2024.2

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：Ventura Beach Marriott, CA   Country：United States  

Event date： 2024.1

Language：Japanese   Presentation type：Poster presentation  

Venue：九州大学筑紫キャンパス，春日   Country：Japan  

Event date： 2024.1

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：九州大学筑紫キャンパス，春日   Country：Japan  

Event date： 2024.1

Language：Japanese   Presentation type：Poster presentation  

Venue：九州大学筑紫キャンパス，春日   Country：Japan  

Event date： 2024.1

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋大学ES総合館ESホール   Country：Japan  

Event date： 2023.12

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：Kyoto International Conference Center   Country：Japan  

Event date： 2023.12

Language：English   Presentation type：Poster presentation  

Country：Japan  

Event date： 2023.12

Language：English   Presentation type：Poster presentation  

Country：Japan  

Event date： 2023.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：早稲田大学、東京   Country：Japan  

Event date： 2023.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：早稲田大学，東京   Country：Japan  

Event date： 2023.11

Language：Japanese   Presentation type：Public lecture, seminar, tutorial, course, or other speech  

Venue：名古屋大学   Country：Japan  

Event date： 2023.9

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：札幌、北海道   Country：Japan  

Event date： 2023.9

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：仙台、宮城   Country：Japan  

Event date： 2023.9

Language：English   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2023.7

Language：English   Presentation type：Oral presentation (general)  

Venue：Sapporo Park Hotel, Sapporo, Japan   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋大学   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Poster presentation  

Venue：Hotel & Resorts SAGA-KARATSU，唐津   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Poster presentation  

Venue：Hotel & Resorts SAGA-KARATSU，唐津   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Poster presentation  

Venue：Hotel & Resorts SAGA-KARATSU，唐津   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Poster presentation  

Venue：Hotel & Resorts SAGA-KARATSU，唐津   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Poster presentation  

Venue：Hotel & Resorts SAGA-KARATSU，唐津   Country：Japan  

Event date： 2023.7

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋大学   Country：Japan  

Event date： 2023.6

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：鈴鹿、三重   Country：Japan  

Event date： 2023.6

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：一橋大学一橋講堂，東京   Country：Japan  

Event date： 2023.6

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Country：Japan  

Event date： 2023.5

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋大学   Country：Japan  

Event date： 2023.5

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Germany  

Event date： 2023.4

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋大学   Country：Japan  

Event date： 2023.4

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：三番町KSビル2F, 東京  

Event date： 2023.3

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：柏、千葉  

Event date： 2023.3

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Event date： 2023.1

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Event date： 2023.1

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：分子科学研究所（明大寺地区キャンパス201），岡崎，愛知  

Event date： 2022.11

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：Nagoya University  

Event date： 2022.11

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：長崎大学  

Event date： 2022.7

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋大学豊田講堂  

Event date： 2021.11

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋   Country：Japan  

Event date： 2021.6

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Venue：名古屋   Country：Japan  

Event date： 2021.3

Language：English   Presentation type：Oral presentation (invited, special)  

Event date： 2021.2

Venue：名古屋商工会議所  

Event date： 2020.7

Venue：名古屋大学  

Event date： 2019.11

Venue：Hiroshima Convention Hall, Hiroshima, Japan  

Event date： 2019.10

Venue：Nanjing University of Technology, Nanjing, China  

Event date： 2019.10

Venue：Soochow University, Suzhou, China  

Event date： 2019.10

Venue：Zejiang University, Hanzhou, China  

Event date： 2019.10

Venue：Nanjing University of Science and Technology, Nanjing, China  

Event date： 2019.8

Venue：定山渓万世閣 ホテルミリオーネ, 札幌，北海道  

Event date： 2019.8

Venue：新化学技術推進協会，東京  

Event date： 2019.7

Venue：ポートメッセなごや，名古屋  

Event date： 2019.7

Venue：ポートメッセなごや，名古屋  

Event date： 2019.7

Venue：Nagoya University  

Event date： 2019.6

Venue：Nagoya University  

Event date： 2019.6

Venue：休暇村支笏湖，北海道  

Event date： 2019.5

Venue：Orakai Songdo Park Hotel、Incheon, Korea  

Event date： 2019.4

Venue：大阪科学技術センター8階大ホール，難波，大阪  

Event date： 2019.2

Venue：名古屋  

Event date： 2019.1

Venue：Münster (University of Münster), Münster, Germany  

Event date： 2019.1

Venue：RWTH Aahen University, Aachen, Germany  

Event date： 2019.1

Venue：Justus–Liebig–Universität Gießen (University of Gießen), Gießen, Germany  

Event date： 2019.1

Venue：Fachbereich Chemie, Phillipps–Universität Marburg (University of Marburg), Marburg, Germany  

Event date： 2018.12

Venue：Chulalongkorn University, Bangkok, Thailand  

Event date： 2018.3

Venue：Tukuba, Japan  

Event date： 2018.3

Venue：OIST, Okinawa, Japan  

Event date： 2018.2

Venue：University of Münster, Münster, Germany  

Event date： 2017.12

Venue：群馬大学，桐生，群馬  

Event date： 2017.10

Venue：京都大学化学研究所，京都  

Event date： 2017.9 - 2019.9

Venue：愛媛大学，松山，愛媛  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (keynote)  

Venue：豊田工業大学８号棟第講義室，名古屋   Country：Japan  

Event date： 2017.3

Venue：JST東京本部別館，市ヶ谷，東京  

Event date： 2017.2

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2017.1

Language：Japanese   Presentation type：Oral presentation (general)  

Event date： 2016.11

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：Howard Civil Service International House, Taipei   Country：Taiwan, Province of China  

Event date： 2016.9

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Country：Japan  

Event date： 2016.6 - 2016.7

Language：English   Presentation type：Oral presentation (invited, special)  

Venue：Seoul, Korea   Country：Korea, Republic of  

Event date： 2016.6

Language：English   Presentation type：Oral presentation (invited, special)  

Event date： 2016.5

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：湯の宿 木もれび，おごと温泉，滋賀   Country：Japan  

Event date： 2016.2

Language：English   Presentation type：Oral presentation (keynote)  

Country：Japan  

Event date： 2015.12

Language：English   Presentation type：Oral presentation (general)  

Country：United States  

Event date： 2015.12

Language：English   Presentation type：Oral presentation (general)  

Country：United Kingdom  

Event date： 2015.11

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Country：Japan  

Event date： 2015.11

Language：English   Presentation type：Oral presentation (invited, special)  

Country：China  

Event date： 2015.10

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Germany  

Event date： 2015.8

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Singapore  

Event date： 2015.6

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Country：Japan  

Event date： 2015.1

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Country：Japan  

Event date： 2014.11

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Japan  

Event date： 2014.11

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Viet Nam  

Event date： 2014.11

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Malaysia  

Event date： 2014.10

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2014.7

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Singapore  

Event date： 2014.7

Language：English   Presentation type：Oral presentation (general)  

Country：Canada  

Event date： 2014.7

Language：English   Presentation type：Oral presentation (invited, special)  

Country：Canada