Updated on 2021/10/25

写真a

 
NAMBO Masakazu
 
Organization
Institute of Transformative Bio-Molecules Designated associate professor
Title
Designated associate professor
Contact information
メールアドレス
External link

Degree 1

  1. 博士(理学) ( 2011.3   名古屋大学 ) 

Research Interests 5

  1. 分子触媒 アリール化 アリールメタン

  2. 炭素-スルホニル結合活性化

  3. 分子触媒

  4. スルホン

  5. アリールメタン

Research Areas 1

  1. Nanotechnology/Materials / Synthetic organic chemistry  / transition metal catalysis

Current Research Project and SDGs 2

  1. 有機硫黄化合物をテンプレートとするアリールアルカン類の効率的合成法の開発

  2. 酸性sp3炭素-水素結合に立脚したアリールメタン類の新規合成法の開発

Research History 10

  1. Nagoya University   Institute of Transformative Bio-Molecules   Designated associate professor

    2021.4

  2. Nagoya University   Institute of Transformative Bio-Molecules   Designated Associate Professor (Co-PI)

    2021.4

  3. Nagoya University   Institute of Transformative Bio-Molecules   Designated Lecturer (Co-PI)

    2018.4 - 2021.3

  4. 名古屋大学トランスフォーマティブ生命分子研究所 特任助教

    2013.2

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    Country:Japan

  5. Nagoya University   Institute of Transformative Bio-Molecules

    2013.2 - 2018.3

  6. 旭化成イーマテリアルズ株式会社勤務

    2011.4 - 2013.1

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    Country:Japan

  7. 旭化成イーマテリアルズ株式会社勤務

    2011.4 - 2013.1

  8. 名古屋大学大学院理学研究科物質理学専攻(化学系)博士課程

    2008.4 - 2011.3

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    Country:Japan

  9. 名古屋大学大学院理学研究科物質理学専攻(化学系)博士課程

    2008.4 - 2011.3

  10. 日本学術振興会 特別研究員(DC1)

    2008.4 - 2011.3

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Education 4

  1. Nagoya University   Graduate School, Division of Natural Science

    2008.4 - 2011.3

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    Country: Japan

  2. Nagoya University   Graduate School of Science   Division of Material Science

    2008.4 - 2011.3

  3. Nagoya University   Graduate School of Science   Division of Material Science

    2006.4 - 2008.3

  4. Nagoya University   Graduate School, Division of Natural Science

    2002.4 - 2006.3

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    Country: Japan

Professional Memberships 5

  1. 日本化学会

  2. KINKA CHEMICAL SOCIETY

  3. THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY

  4. 日本化学会

  5. THE SOCIETY OF FLUORINE CHEMISTRY

Committee Memberships 2

  1. 名古屋大学理学部   同窓会報編集委員  

    2018.4   

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    Committee type:Other

  2. 名古屋大学理学部   同窓会評議員  

    2013.4   

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    Committee type:Other

Awards 13

  1. Chemist Award BCA

    2021.10   MSD Life Science Founddation  

    Masakazu Nambo

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    Award type:Award from Japanese society, conference, symposium, etc. 

  2. Incentive Award in Synthetic Organic Chemistry, Japan

    2020.12   The Society of Synthetic Organic Chemistry, Japan  

    Masakazu Nambo

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    Award type:Award from Japanese society, conference, symposium, etc. 

  3. 第99春季年会 優秀講演賞(学術)

    2019.5   日本化学会  

    南保 正和

  4. The Chemical Society of Japan, Lecture Award for Young Chemists

    2018.3  

    NAMBO Masakazu

  5. SYNLETT Best Paper Award 2017

    2018.1   Thieme Chemistry  

    NAMBO Masakazu

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    Award type:International academic award (Japan or overseas) 

  6. The 4th ITbM Research Award

    2018.1  

    NAMBO Masakazu

  7. 日本化学会第96春季年会 優秀講演賞(学術)

    2016.5   日本化学会  

    南保正和

  8. 第3回ITbM Research Award

    2016.1   トランスフォーマティブ生命分子研究所  

    南保 正和

  9. 第28回有機合成化学協会研究企画賞(中外製薬)

    2015.2   有機合成化学協会  

    南保 正和

  10. Inoue Research Award for Young Scientists

    2014.2  

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    Country:Japan

  11. 第1回ITbM Research Award

    2013.1   トランスフォーマティブ生命分子研究所  

    南保 正和

  12. The Japanese-German Graduate Externship, DFG opening ceremony, representative presentation

    2011.5  

    NAMBO Masakazu

  13. The 54th Symposium on Organometallic Chemistry, poster award

    2008.1  

    NAMBO Masakazu

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Papers 34

  1. Transition Metal-Catalyzed Cross-Couplings of Benzylic Sulfone Derivatives Reviewed

    Nambo Masakazu, Crudden Cathleen M.

    CHEMICAL RECORD     2021.9

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

    DOI: 10.1002/tcr.202100210

    Web of Science

    PubMed

  2. Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane Reviewed

    Joshua J. Clarke, Yuuki Maekawa, Masakazu Nambo, Cathleen M. Crudden

    Organic Letters   Vol. 23 ( 17 ) page: 6617 - 6621   2021.9

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

    DOI: 10.1021/acs.orglett.1c01892

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  3. Synthesis and enantioseparation of chiral Au13 nanoclusters protected by bis-N-heterocyclic carbene ligands Reviewed

    Hong Yi, Kimberly M. Osten, Tetyana I. Levchenko, Alex J. Veinot, Yoshitaka Aramaki, Takashi Ooi, Masakazu Nambo, Cathleen M. Crudden

    Chemical Science   Vol. 12 ( 31 ) page: 10436 - 10440   2021.8

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    Authorship:Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>A series of chiral Au<sub>13</sub> nanoclusters were synthesized <italic>via</italic> the direct reduction of achiral dinuclear Au(<sc>i</sc>) halide complexes ligated by <italic>ortho</italic>-xylyl-linked bis-<italic>N</italic>-heterocyclic carbene (NHC) ligands.</p>

    DOI: 10.1039/d1sc03076k

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  4. Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones Reviewed

    Masakazu Nambo, Yasuyo Tahara, Jacky C.-H. Yim, Daisuke Yokogawa, Cathleen M. Crudden

    Chemical Science   Vol. 12 ( 13 ) page: 4866 - 4871   2021.4

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    Authorship:Lead author, Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>A new method for the generation of tertiary radicals through single electron reduction of alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed.</p>

    DOI: 10.1039/d1sc00133g

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  5. Alkyltriflones in the Ramberg–Bäcklund Reaction: An Efficient and Modular Synthesis of gem-Difluoroalkenes Reviewed

    Yuuki Maekawa, Masakazu Nambo, Daisuke Yokogawa, Cathleen M. Crudden

    Journal of the American Chemical Society   Vol. 142 ( 37 ) page: 15667 - 15672   2020.9

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    Authorship:Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

    DOI: 10.1021/jacs.0c07924

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  6. Synthesis and properties of an Au6 cluster supported by a mixed N-heterocyclic carbene–thiolate ligand Reviewed

    Kirsi Salorinne, Renee W. Y. Man, Paul A. Lummis, Maryam Sabooni Asre Hazer, Sami Malola, Jacky C.-H. Yim, Alex J. Veinot, Wenxia Zhou, Hannu Häkkinen, Masakazu Nambo, Cathleen M. Crudden

    Chemical Communications   Vol. 56 ( 45 ) page: 6102 - 6105   2020.6

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    Authorship:Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/d0cc01482f

    Web of Science

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  7. Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling Reviewed

    Masakazu Nambo, Jacky C.-H. Yim, Luiza B. O. Freitas, Yasuyo Tahara, Zachary T. Ariki, Yuuki Maekawa, Daisuke Yokogawa, Cathleen M. Crudden

    Nature Communications   Vol. 10 ( 1 ) page: 4528   2019.12

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media {LLC}  

    DOI: 10.1038/s41467-019-11758-w

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  8. Pyridine-catalyzed desulfonative borylation of benzyl sulfones Reviewed

    Yuuki Maekawa, Zachary T. Ariki, Masakazu Nambo, Cathleen M. Crudden

    Organic & Biomolecular Chemistry   Vol. 17 ( 31 ) page: 7300 - 7303   2019.8

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    Authorship:Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/c9ob01099h

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  9. Copper-catalyzed Desulfonylative Cross-coupling of Benzhydryl Sulfones with Azoles Reviewed

    Yim Jacky C-H, Nambo Masakazu, Tahara Yasuyo, Crudden Cathleen M

    CHEMISTRY LETTERS   Vol. 48 ( 8 ) page: 975 - 977   2019.8

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

    DOI: 10.1246/cl.190334

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  10. N-heterocyclic carbene-functionalized magic-number gold nanoclusters Reviewed

    Mina R. Narouz, Kimberly M. Osten, Phillip J. Unsworth, Renee W.Y. Man, Kirsi Salorinne, Shinjiro Takano, Ryohei Tomihara, Sami Kaappa, Sami Malola, Cao Thang Dinh, J. Daniel Padmos, Kennedy Ayoo, Patrick J. Garrett, Masakazu Nambo, J. Hugh Horton, Edward H. Sargent, Hannu Häkkinen, Tatsuya Tsukuda, Cathleen M. Crudden

    Nature Chemistry   Vol. 11 ( 5 ) page: 419 - 425   2019.5

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

    © 2019, The Author(s), under exclusive licence to Springer Nature Limited. Magic-number gold nanoclusters are atomically precise nanomaterials that have enabled unprecedented insight into structure–property relationships in nanoscience. Thiolates are the most common ligand, binding to the cluster via a staple motif in which only central gold atoms are in the metallic state. The lack of other strongly bound ligands for nanoclusters with different bonding modes has been a significant limitation in the field. Here, we report a previously unknown ligand for gold(0) nanoclusters—N-heterocyclic carbenes (NHCs)—which feature a robust metal–carbon single bond and impart high stability to the corresponding gold cluster. The addition of a single NHC to gold nanoclusters results in significantly improved stability and catalytic properties in the electrocatalytic reduction of CO 2 . By varying the conditions, nature and number of equivalents of the NHC, predominantly or exclusively monosubstituted NHC-functionalized clusters result. Clusters can also be obtained with up to five NHCs, as a mixture of species.

    DOI: 10.1038/s41557-019-0246-5

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  11. Cu‐Catalyzed Desulfonylative Amination of Benzhydryl Sulfones Reviewed

    Masakazu Nambo, Yasuyo Tahara, Jacky C.‐H. Yim, Cathleen M. Crudden

    Chemistry – A European Journal   Vol. 25 ( 8 ) page: 1923 - 1926   2019.2

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    Authorship:Lead author, Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/chem.201805638

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  12. Ultrastable Gold Nanoparticles Modified by Bidentate N-Heterocyclic Carbene Ligands Reviewed

    Renee W. Y. Man, Chien-Hung Li, Michael W. A. MacLean, Olena V. Zenkina, Matthew T. Zamora, Lisa N. Saunders, Alexander Rousina-Webb, Masakazu Nambo, Cathleen M. Crudden

    Journal of the American Chemical Society   Vol. 140 ( 5 ) page: 1576 - 1579   2018.2

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

    Highly stable gold nanoparticles (Au NPs) functionalized by bidentate N-heterocyclic carbene (NHC) ligands have been synthesized by top-down and bottom-up approaches. A detailed study of the effect of alkylation, denticity, and method of synthesis has led to the production of NHC-stabilized nanoparticles with higher thermal stability than bi- and tridentate thiol-protected Au NPs and than monodentate NHC-stabilized NPs. Importantly, bidentate NHC-protected NPs also displayed unprecedented stability to external thiol, which has been an unsolved problem to date with all nanoparticles. Thus, multidentate NHC ligands are an important, and as yet unrecognized, step forward for the preparation of high stability nanomaterials.

    DOI: 10.1021/jacs.7b08516

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  13. Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Tertiary Sulfones Reviewed

    Zachary T. Ariki, Yuuki Maekawa, Masakazu Nambo, Cathleen M. Crudden

    Journal of the American Chemical Society   Vol. 140 ( 1 ) page: 78 - 81   2018.1

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

    We describe the development of a nickel-catalyzed Suzuki-Miyaura cross-coupling of tertiary benzylic and allylic sulfones with arylboroxines. A variety of tertiary sulfones, which can easily be prepared via a deprotonation-alkylation route, were reacted to afford symmetric and unsymmetric quaternary products in good yields. We highlight the use of either BrettPhos or Doyle's phosphines as effective ligands for these challenging desulfonative coupling reactions. The utility of this methodology was demonstrated in the concise synthesis of a vitamin D receptor modulator analogue.

    DOI: 10.1021/jacs.7b10855

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  14. Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes Reviewed

    Masakazu Nambo, Jacky C. -H. Yim, Kevin G. Fowler, Cathleen M. Crudden

    SYNLETT   Vol. 28 ( 20 ) page: 2936 - 2940   2017.12

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

    The formal cross-dehydrogenative coupling of triarylmethanes with arenes promoted by triflic acid and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is described. This method provides a variety of tetraarylmethane derivatives in good to excellent yields from triarylmethanes that can be readily prepared by our previous methods. Control experiments suggest a possible catalytic cycle involving the generation of a trityl cation intermediate followed by nucleophilic addition of the arene.

    DOI: 10.1055/s-0036-1588563

    Web of Science

  15. Pd-Catalyzed Desulfonative Cross-Coupling of Benzylic Sulfone Derivatives with 1,3-Oxazoles Reviewed

    Jacky C.-H. Yim, Masakazu Nambo, Cathleen M. Crudden

    Organic Letters   Vol. 19 ( 14 ) page: 3715 - 3718   2017.7

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

    The Pd-catalyzed desulfonative cross-coupling reaction of benzylic sulfone derivatives with 1,3-oxazoles via a deprotonative pathway has been developed. Broad substrate scope for both sulfone and 1,3-oxazole partners is observed, affording a variety of 1,3-oxazole-containing triarylmethanes. Sulfone partners that are primary benzylic, secondary benzylic, and benzhydryl are all effective. Using this method, the straightforward synthesis of multiply arylated structures has been demonstrated.

    DOI: 10.1021/acs.orglett.7b01510

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  16. Water-Soluble N-Heterocyclic Carbene-Protected Gold Nanoparticles: Size-Controlled Synthesis, Stability, and Optical Properties Reviewed

    Salorinne, Kirsi, Man, Renee W. Y., Li, Chien-Hung, Taki, Masayasu, Nambo, Masakazu, Crudden, Cathleen M.

    Angewandte Chemie-International Edition   Vol. 56 ( 22 ) page: 6198 - 6202   2017.5

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

    NHC-Au-I complexes were used to prepare stable, water-soluble, NHC-protected gold nanoparticles. The water-soluble, charged nature of the nanoparticles permitted analysis by polyacrylamide gel electrophoresis (PAGE), which showed that the nanoparticles were highly monodisperse, with tunable core diameters between 2.0 and 3.3 nm depending on the synthesis conditions. Temporal, thermal, and chemical stability of the nanoparticles were determined to be high. Treatment with thiols caused etching of the particles after 24 h; however larger plasmonic particles showed greater resistance to thiol treatment. These water-soluble, bio-compatible nanoparticles are promising candidates for use in photoacoustic imaging, with even the smallest nanoparticles giving reliable photoacoustic signals.

    DOI: 10.1002/anie.201701605

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  17. Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions Reviewed

    Nambo, Masakazu, Keske, Eric C., Rygus, Jason P. G., Yim, Jacky C. -H., Crudden, Cathleen M.

    Acs Catalysis   Vol. 7 ( 2 ) page: 1108 - 1112   2017.2

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

    The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring of the sulfone facilitates the Pd-catalyzed activation of C-SO2 bonds. Cross-coupling reactions with fluorinated sulfone electrophiles are reported, leading to a variety of multiply arylated products in good yields. The reactivity of this unusual electrophile is benchmarked versus common electrophiles and its use in iterative cross-couplings for concise synthesis of biologically active molecules is described.

    DOI: 10.1021/acscatal.6b03434

    Web of Science

  18. Combination of Synthetic Chemistry and Live-Cell Imaging Identified a Rapid Cell Division Inhibitor in Tobacco and Arabidopsis thaliana Reviewed

    Nambo, Masakazu, Kurihara, Daisuke, Yamada, Tomomi, Nishiwaki-Ohkawa, Taeko, Kadofusa, Naoya, Kimata, Yusuke, Kuwata, Keiko, Umeda, Masaaki, Ueda, Minako

    Plant and Cell Physiology   Vol. 57 ( 11 ) page: 2255 - 2268   2016.11

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

    Cell proliferation is crucial to the growth of multicellular organisms, and thus the proper control of cell division is important to prevent developmental arrest or overgrowth. Nevertheless, tools for controlling cell proliferation are still poor in plant. To develop novel tools, we focused on a specific compound family, triarylmethanes, whose members show various antiproliferative activities in animals. By combining organic chemistry to create novel and diverse compounds containing the triarylmethyl moiety and biological screens based on live-cell imaging of a fluorescently labeled tobacco Bright Yellow-2 (BY-2) culture cell line (Nicotiana tabacum), we isolated (3-furyl)diphenylmethane as a strong but partially reversible inhibitor of plant cell division. We also found that this agent had efficient antiproliferative activity in developing organs of Arabidopsis thaliana without causing secondary defects in cell morphology, and induced rapid cell division arrest independent of the cell cycle stage. Given that (3-furyl)diphenylmethane did not affect the growth of a human cell line (HeLa) and a budding yeast (Saccharomyces cerevisiae), it should act specifically on plants. Taking our results together, we propose that the combination of desired chemical synthesis and detailed biological analysis is an effective tool to create novel drugs, and that (3-furyl)diphenylmethane is a specific antiproliferative agent for plants.

    DOI: 10.1093/pcp/pcw140

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  19. Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate Reviewed

    Nambo, Masakazu, Ariki, Zachary T., Canseco-Gonzalez, Daniel, Beattie, D. Dawson, Crudden, Cathleen M.

    Organic Letters   Vol. 18 ( 10 ) page: 2339 - 2342   2016.5

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

    A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.

    DOI: 10.1021/acs.orglett.6b00744

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  20. Iterative protecting group-free cross-coupling leading to chiral multiply arylated structures Reviewed

    Crudden, Cathleen M., Ziebenhaus, Christopher, Rygus, Jason P. G., Ghozati, Kazem, Unsworth, Phillip J., Nambo, Masakazu, Voth, Samantha, Hutchinson, Marieke, Laberge, Veronique S., Maekawa, Yuuki, Imao, Daisuke

    Nature Communications   Vol. 7   page: 11065   2016.4

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

    The Suzuki-Miyaura cross-coupling is one of the most often utilized reactions in the synthesis of pharmaceutical compounds and conjugated materials. In its most common form, the reaction joins two sp(2)-functionalized carbon atoms to make a biaryl or diene/polyene unit. These substructures are widely found in natural products and small molecules and thus the Suzuki-Miyaura cross-coupling has been proposed as the key reaction for the automated assembly of such molecules, using protecting group chemistry to affect iterative coupling. We present herein, a significant advance in this approach, in which multiply functionalized cross-coupling partners can be employed in iterative coupling without the use of protecting groups. To accomplish this, the orthogonal reactivity of different boron substituents towards the boron-to-palladium transmetalation reaction is exploited. The approach is illustrated in the preparation of chiral enantioenriched compounds, which are known to be privileged structures in active pharmaceutical compounds.

    DOI: 10.1038/ncomms11065

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  21. Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis Reviewed

    Nambo, Masakazu, Crudden, Cathleen M.

    Acs Catalysis   Vol. 5 ( 8 ) page: 4734 - 4742   2015.8

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

    Triarylmethanes and related compounds are fascinating molecules because of their structural and physical properties, many potential applications in organic functional materials, and high biological activity. Recently, catalysis has provided new synthesis routes to triarylmethanes with high selectivity and diversity, including the possibility of preparing enantiomerically enriched derivatives, which is typically challenging using classical methods. This Perspective reviews recent advances in new synthesis approaches to triarylmethanes using well-defined catalysts. These methods will allow the development of new, unexplored triarylmethane structures.

    DOI: 10.1021/acscatal.5b00909

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  22. The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes Reviewed

    Nambo, Masakazu, Yar, Muhammad, Smith, Joel D., Crudden, Cathleen M.

    Organic Letters   Vol. 17 ( 1 ) page: 50 - 53   2015.1

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

    The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials.

    DOI: 10.1021/ol503213z

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  23. Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone Reviewed

    Nambo Masakazu, Crudden Cathleen M.

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 53 ( 3 ) page: 742 - 746   2014.1

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

    DOI: 10.1002/anie.201307019

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  24. Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone. Reviewed

    Nambo M, Crudden CM

    Angewandte Chemie (International ed. in English)   Vol. 53 ( 3 ) page: 742 - 6   2014.1

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

    DOI: 10.1002/anie.201307019

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  25. Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone Reviewed

    Masakazu Nambo, Cathleen M. Crudden

    Angewandte Chemie International Edition   Vol. 53 ( 3 ) page: 742-746   2014.1

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

    Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals.

  26. Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone Reviewed

    Nambo, Masakazu, Crudden, Cathleen M.

    Angewandte Chemie-International Edition   Vol. 53 ( 3 ) page: 742 - 746   2014

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

    Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals.

    DOI: 10.1002/anie.201307019

    Web of Science

  27. Palladium-catalyzed tetraallylation of C-60 with allyl chloride and allylstannane: mechanism, regioselectivity, and enantioselectivity Reviewed

    Nambo, Masakazu, Wakamiya, Atsushi, Itami, Kenichiro

    Chemical Science   Vol. 3 ( 12 ) page: 3474 - 3481   2012.12

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

    We have established a unique Pd-catalyzed tetraallylation of C-60 with allyl chloride and allylstannane that likely proceeds by the action of amphiphilic bis(pi-ally)palladium. Mechanistic analysis has revealed that both steric (for the first diallylation) and electronic (for the second diallylation) factors are responsible for high regioselectivity. The ring-closing metathesis reaction and hydrogenation of the tetraallylated product took place in the presence of Ru and Rh catalysts. Moreover, we found that chiral phosphoramidites are effective chiral ligands for the enantioselective tetraallylation of C-60. Pronounced enantioselectivity up to 88% ee was realized in the production of tetraallylated C-60.

    DOI: 10.1039/c2sc21126b

    Web of Science

  28. Aziridinofullerene: A Versatile Platform for Functionalized Fullerenes Reviewed

    Nambo, Masakazu, Segawa, Yasutomo, Itami, Kenichiro

    Journal of the American Chemical Society   Vol. 133 ( 8 ) page: 2402 - 2405   2011.3

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

    An aziridine moiety on the fullerene core can serve as an acid-triggered reacting template for the controlled synthesis of a range of functionalized fullerenes that are otherwise difficult to synthesize in an efficient and selective manner. A copper-catalyzed aziridination of C-60 for the practical synthesis of aziridinofullerene 1 and acid-catalyzed reactions of 1 with mono- and bifunctional nucleophiles as well as alkynes are described. The rapid generation of structural diversity in a single chemical operation using the common platform 1 is notable.

    DOI: 10.1021/ja111213k

    Web of Science

    PubMed

  29. Selective Introduction of Organic Groups to C-60 and C-70 Using Organoboron Compounds and Rhodium Catalyst: A New Synthetic Approach to Organo(hydro)fullerenes Reviewed

    Nambo, Masakazu, Segawa, Yasutomo, Wakamiya, Atsushi, Itami, Kenichiro

    Chemistry-an Asian Journal   Vol. 6 ( 2 ) page: 590 - 598   2011.2

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

    A Rh-catalyzed reaction of C-60 and C-70 with organoboron compounds is described. This new catalytic method enables introduction of various organic groups onto C-60 and C-70. [Rh-(cod) (MeCN)(2)]BF4 proved to be the most effective catalyst in terms of productivity and selectivity. The reaction generally proceeds with a high regioselectivity and in a mono-addition selective manner. It was found that water is an essential additive to promote the reaction. By X-ray crystal structure analysis, we have confirmed the reaction site of organometallic-based hydroarylation of C-70 for the first time. Various functional fullerenes, such as fullerene-tagged amino acids and fullerene-capped pi systems, can be synthesized. The X-ray crystal structure of biphenyl-attached C-60 revealed an interesting opportunity for the well-organized alignment of bucky balls by taking advantage of CH-pi interactions.

    DOI: 10.1002/asia.201000583

    Web of Science

    PubMed

  30. Regioselective Unsymmetrical Tetraallylation of C-60 through Palladium Catalysis Reviewed

    Masakazu Nambo, Atsushi Wakamiya, Shigehiro Yamaguchi, Kenichiro Itami

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 131 ( 42 ) page: 15112 - +   2009.10

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

    A Pd-catalyzed tetraallylation of C-60 that selectively occurs with an unsymmetrical addition pattern has been established. Treatment of C-60 with CH2=CHCH2Cl, CH2=CHCH2SnBu3, and PdCl2[P(OPh)(3)](2) in 1,2-Cl2C6H4 at 50 degrees C afforded the tetraallylated fullerene in 74% yield with virtually complete regioselectivity. Mechanistic investigations showed that (i) tetraallylation proceeds through consecutive nucleophilic/electrophilic allylations [Likely via a bis(pi-allyl)palladium intermediate] and (ii) both steric (for the first diallylation) and electronic (for the second diallylation) factors are responsible for the high regioselectivity.

    DOI: 10.1021/ja9071173

    Web of Science

    PubMed

  31. Palladium-Catalyzed Carbon-Carbon Bond Formation and Cleavage of Organo(hydro)fullerenes Reviewed

    Nambo, Masakazu, Itami, Kenichiro

    Chemistry-a European Journal   Vol. 15 ( 19 ) page: 4760 - 4764   2009

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

    DOI: 10.1002/chem.200900022

    Web of Science

    PubMed

  32. Structure-affinity-relationship study of bicyclic σ receptor ligands Reviewed

    Ralph Holl, Christian Geiger, Masakazu Nambo, Kenichiro Itami, Dirk Schepmann, Bernhard Wünsch

    Central Nervous System Agents in Medicinal Chemistry   Vol. 9 ( 3 ) page: 220 - 229   2009

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Bentham Science Publishers B.V.  

    It was postulated that N6-allyl bicyclic derivatives 1 bind with N-8 at the proton donor site of the σ1 receptor and that a substituent in 2-position of the bicyclic framework 1 results in unfavorable steric interactions with the σ1 receptor protein. In order to support this hypothesis both enantiomers of 6-allyl-8-(4-methoxybenzyl)-6,8- diazabicyclo[3.2.2]non-2-ene (2/ent-2) and 6-benzyl-8-(4-methoxybenzyl)-6,8- diazabicyclo[3.2.2]nonane 3/ent-3 were synthesized stereoselectively. The (S,S)-configured enantiomers 2 and 3 are the eutomers with eudismic ratios of 31 and 4.8, respectively. Therefore, these enantiomers are used in the σ1 pharmacophore model. The N6-allyl derivative 2 with a double bond in the three carbon bridge adopts the orientation 2c with N-8 interacting with the σ1 receptor proton donor site (Fig. 2) resulting in slightly reduced steric interactions of the small double bond in 2/3-position. The almost C2-symmetric benzyl derivative 3 can adopt both orientations 2c and 2d at the σ1 receptor (N-8 or N-6 interacts with the σ1 receptor proton donor site) resulting in subnanomolar σ1 receptor affinity (Ki = 0.91 nM). © 2009 Bentham Science Publishers Ltd.

    DOI: 10.2174/1871524910909030220

    Scopus

    PubMed

    Other Link: http://orcid.org/0000-0003-0153-3178

  33. A Bench-Stable Pd Catalyst for the Hydroarylation of Fullerene with Boronic Acids Reviewed

    Susumu Mori, Masakazu Nambo, Liang-Chen Chi, Jean Bouffard, Kenichiro Itami

    ORGANIC LETTERS   Vol. 10 ( 20 ) page: 4609 - 4612   2008.10

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

    A Pd(II) catalyst for the hydroarylation of fullerene with boronic acids is presented. Treatment of C(60) with an arylboronic acid in the presence of a catalytic amount of Pd(2-PyCH=NPh)(OCOC(6)F(5))(2) in H(2)O/1,2-Cl(2)C(6)H(4) at room temperature furnishes the hydroarylation product (Ar-C(60)-H) in good yield with high selectivity. This complex possesses high catalytic activity paired with bench stability in the solid state.

    DOI: 10.1021/ol801936j

    Web of Science

    PubMed

  34. Rh-catalyzed arylation and alkenylation of C-60 using organoboron compounds Reviewed

    Masakazu Nambo, Ryoji Noyori, Kenichiro Itami

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 129 ( 26 ) page: 8080 - +   2007.7

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

    A new organoboron-based arylation and alkenylation of C-60 catalyzed by a rhodium complex was developed. A treatment of C-60 with an organoboron compound in the presence of a catalytic amount of [Rh(cod)(CH3CN)(2)]BF4 in H2O/1,2-Cl2C6H4 furnished a functionalized fullerene (R-C-60-H) with good to excellent selectivity. Aryl, heteroaryl, and alkenyl groups can be installed by the reactions using the corresponding boronic acids, pinacol esters, and potassium trifluoroborates.

    DOI: 10.1021/ja073042x

    Web of Science

    PubMed

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Books 6

  1. スルホンを用いる新しいクロスカップリング反応と応用

    南保正和( Role: Sole author)

    化学と教育, 68巻8号, p344-347.  2020.8 

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    Language:Japanese

  2. 第三級アルキルホウ素化合物の触媒的変換反応

    南保正和( Role: Sole author)

    Organometallic News, Vol.1, p26  2020.3 

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    Language:Japanese

  3. スルホンの特性を活かしたアリールメタン類の迅速合成

    南保 正和( Role: Sole author)

    化学と工業  2018.8 

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    Language:Japanese

  4. SYNLETT Best Paper Award 2017: Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes

    NAMBO Masakazu( Role: Joint author)

    Synform  2018.6 

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    Language:Japanese

  5. Synthesis of New Nano Carbon Materials

    Masakazu Nambo, Kenichiro Itami( Role: Joint author)

    McGraw-Hill Yearbook of Science & Technology  2009 

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    Language:English

  6. Synthesis of New Nano Carbon Materials

    Masakazu Nambo, Kenichiro Itami( Role: Joint author)

    McGraw-Hill Yearbook of Science & Technology  2009 

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    Responsible for pages:379   Language:English

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MISC 3

  1. Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone Reviewed

    Masakazu Nambo, Cathleen M. Crudden

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 53 ( 3 ) page: 742 - 746   2014.1

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

    Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals.

    DOI: 10.1002/anie.201307019

    Web of Science

  2. Pd触媒によるC<sub>60</sub>の位置選択的テトラアリル化反応

    南保正和, 若宮淳志, 山口茂弘, 伊丹健一郎

    日本化学会講演予稿集   Vol. 90th ( 4 ) page: 1152   2010.3

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    Language:Japanese  

    J-GLOBAL

  3. Synthesis of New Nano Carbon Materials Invited

    Masakazu Nambo, Kenichiro Itami

    McGraw-Hill Yearbook of Science & Technology     page: 379-381   2009

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    Language:English   Publishing type:Article, review, commentary, editorial, etc. (scientific journal)  

Presentations 23

  1. New Transformations of Sulfones inspired by C–H Functionalization Invited

    Masakazu Nambo

    12th CCHF Annual Meeting  2020.9.18 

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    Event date: 2020.9

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

  2. Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of -Fluorinated Benzylic Triflones Invited

    Masakazu Nambo

    Tateshina Conference on Organic Chemistry  2019.11.9 

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    Event date: 2019.11

    Language:English   Presentation type:Poster presentation  

  3. Pd-Catalyzed Desulfonative Cross-Coupling Reactions of Fluorinated Sulfone Derivatives

    Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden

    2017.11.14 

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    Language:Japanese   Presentation type:Poster presentation  

  4. Pd-Catalyzed Arylation of Methyl Sulfone Derivatives via C–SO2 Activation: Mechanistic Studies and Applicatio

    Masakazu Nambo, Kohsuke Usui, Daisuke Yokogawa, Jacky C.-H. Yim, Cathleen M. Crudden

    第64回有機金属化学討論会  2017.9.7 

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    Language:Japanese   Presentation type:Oral presentation (general)  

  5. Pd- and Ni-Catalyzed Desulfonylative Cross-Coupling Reactions of Benzylic Sulfone Derivatives International conference

    Masakazu Nambo, Jacky C.-H. Yim, Zachary T. Ariki, Yuuki Maekawa, Cathleen M. Crudden

    28th International Symposium on the Organic Chemistry of Sulfur (ISOCS-28)  2018.8.27 

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    Language:English   Presentation type:Oral presentation (general)  

  6. New Chemical Transformations of Organosulfones through C–SO2 Activation Invited

    NAMBO Masakazu

    2018.3.20 

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

  7. Modular Synthesis of Multiply-arylated Alkanes through Desulfonylative Cross-Coupling Reactions International conference

    Masakazu Nambo, Jacky C.-H. Yim, Zachary T. Ariki, Yuuki Maekawa, Kevin G. Fowler, Cathleen M. Crudden

    International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)  2018.8.25 

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    Language:English   Presentation type:Oral presentation (general)  

  8. Modular Synthesis of Multiply-arylated Alkanes through Desulfonylative Cross-Coupling Reactions International conference

    Masakazu Nambo, Jacky C.-H. Yim, Zachary T. Ariki, Yuuki Maekawa, Kevin G. Fowler, Cathleen M. Crudden

    2018.11.1 

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    Language:English   Presentation type:Poster presentation  

  9. Modular Synthesis of Fluorinated Arylmethane Derivatives through Desulfonylative Reactions International conference

    Masakazu Nambo, Yasuyo Tahara, Jacky C.-H. Yim, Luiza B, O. Freitas, Yuuki Maekawa, Zachary T. Ariki, Cathleen M. Crudden

    The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)  2018.11.14 

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    Language:English   Presentation type:Poster presentation  

  10. Desulfonylative Transformations of a-Fluorinated Benzylic Sulfones

    NAMBO Masakazu

    2019.3.16 

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    Language:English   Presentation type:Oral presentation (general)  

  11. Cu-Catalyzed Desulfonylative Amination of Benzhydryl Sulfone Derivatives via a Cu-Carbene Intermediate

    Masakazu Nambo, Yasuyo Tahara, Jacky C.-H. Yim, Cathleen M. Crudden

    2018.9.20 

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    Language:Japanese   Presentation type:Oral presentation (general)  

  12. Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of a-Fluorinated Benzylic Triflones

    NAMBO Masakazu

    2019.9.14 

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    Language:Japanese   Presentation type:Oral presentation (general)  

  13. 古くて新しい炭素–スルホニル結合活性化反応の開発

    南保 正和

    有機金属若手の会  2019.9.13 

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

  14. Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of a-Fluorinated Benzylic Triflones International conference

    NAMBO Masakazu

    27th International Society of Heterocyclic Chemistry Congress  2019.9.1 

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    Language:English   Presentation type:Poster presentation  

  15. Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes International conference

    Masakazu Nambo, Eric, C. Keske, Jason, P. G. Ryugus, Jacky C.-H. Yim, Cathleen M. Crudden

    2015.12.18 

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    Language:English   Presentation type:Oral presentation (general)  

  16. Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone

    NAMBO Masakazu

    IGER International Symposium on Chemical Science in Asia  2014.5.26 

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    Language:English   Presentation type:Poster presentation  

  17. Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone

    NAMBO Masakazu

    2014.3.28 

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    Language:English   Presentation type:Oral presentation (general)  

  18. Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone International conference

    NAMBO Masakazu

    The 2nd International Symposium on Transformative Bio-Molecules  2014.5.12 

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    Language:English   Presentation type:Poster presentation  

  19. Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes

    Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden

    Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes  2016.9.16 

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    Language:Japanese   Presentation type:Poster presentation  

  20. Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone

    NAMBO Masakazu

    2014.9.26 

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    Language:Japanese   Presentation type:Poster presentation  

  21. The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation

    Masakazu Nambo, Muhammad Yar, Joel, D. Smith, Cathleen M. Crudden

    2015.3.26 

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    Language:English   Presentation type:Oral presentation (general)  

  22. Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes International conference

    Masakazu Nambo, Eric, C. Keske, Jason, P. G. Ryugus, Jacky C.-H. Yim, Cathleen M. Crudden

    Gordon Research Conference, Stereochemistry  2016.7.27 

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    Language:English   Presentation type:Poster presentation  

  23. Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes

    Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden

    2016.3.25 

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Research Project for Joint Research, Competitive Funding, etc. 2

  1. 炭素–水素結合の化学変換のみを基軸とする逐次的アリール化反応の開発と生物活性化合物創製への展開

    2014.10 - 2015.10

    学内共同研究 

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    本研究では、生物活性化合物に頻繁にみられるトリアリールメタン化合物群の直接的合成手法の確立を目的とする。具体的には、メチルスルホン化合物の有する特異な酸性sp3炭素—水素(C–H)結合とスルホニル基の潜在的な脱離基としての特性に着目し、連続的なC–Hアリール化を可能にする新触媒の開発を行う。開発した手法を駆使し、抗癌剤として注目されているトリアリールメタン骨格を有する化合物群の最短工程かつ効率的な合成を達成する。

  2. 多置換アリールメタン類の迅速構築法の開発と生物活性化合物合成への応用

    2013.10 - 2014.10

    学内共同研究 

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    本研究では、生物活性化合物に頻繁にみられるアリールメタン化合物群の一般的合成手法の確立を目的とする。具体的には、電子求引基に置換されたメタン化合物の有する酸性sp3炭素—水素(C–H)結合に着目し、芳香族ハロゲン化物とのC–Hアリール化を可能にする新触媒の開発を行う。さらに開発した手法を連続的な芳香環導入反応へと展開するとともに、甲状腺ホルモンや抗癌剤として注目されている多置換アリールメタン骨格を有する化合物群の最短工程かつ効率的な合成を達成する。メチル基をプラットホームとしてアリール基を自在に導入する手法は生物活性化合物群を構築していく上で強力な合成手法となることは明白であり、本研究の達成によって、生物活性化合物群の迅速供給を可能にするのみならず、分子触媒化学においても新しい指針を示す極めてインパクトの大きな研究に発展すると確信する

KAKENHI (Grants-in-Aid for Scientific Research) 20

  1. 動的エキシトンを利用する可視光駆動型ラジカル発生法の開発

    Grant number:21H05390  2021.9 - 2023.3

    科学研究費助成事業  学術変革領域研究(A)

    南保 正和

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    Authorship:Principal investigator 

    Grant amount:\7800000 ( Direct Cost: \6000000 、 Indirect Cost:\1800000 )

  2. Generation of radical species by the design of sulfonyl groups

    Grant number:21K05068  2021.4 - 2024.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

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    Authorship:Principal investigator 

    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

  3. 脂質代謝疾患の克服を指向した新規甲状腺ホルモン誘導体の開発

    2020.10 - 2021.9

    公益財団法人 薬理研究会  研究助成金 

    南保正和

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    Authorship:Principal investigator 

  4. 植物ホルモンフローアトラスの構築

    2019.10 - 2024.3

    国立研究開発法人 科学技術振興機構  多細胞間での時空間的な相互作用の理解を目指した技術・解析基盤の創出 

    土屋雄一郎, 南保正和, 佐藤良勝, 土方優

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    Authorship:Coinvestigator(s) 

  5. 金属-カルベン種の新規発生法の開拓と精密分子変換への応用

    2019.4 - 2021.3

    公益財団法人 立松財団  研究助成金 

    南保正和

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    Authorship:Principal investigator 

  6. 甲状腺ホルモンのβ受容体選択的な新規アゴニストの創製

    2019.4 - 2020.3

    公益財団法人 中冨健康科学振興財団  研究助成金 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  7. 炭素–スルホニル結合活性化戦略に基づく含窒素化合物の自在合成法の開発

    2018.4 - 2019.3

    公益財団法人 市原国際奨学財団  研究助成金 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  8. Development of enantioselective cross-coupling based on dynamic kinetic resolution

    Grant number:17K17805  2017.4 - 2020.3

    Nambo Masakazu

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    Authorship:Principal investigator 

    Grant amount:\4290000 ( Direct Cost: \3300000 、 Indirect Cost:\990000 )

    We have found the dynamic kinetic asymmetric cross-coupling reactions using organosulfones for the synthesis of enantio-enriched triarylmethane derivatives. During the course of this study, Cu-catalyzed amination of benzhydrylsulfones through the Cu-carbene intermediate and Pd-catalyzed desulfonylative cross-coupling reactions of a-fluorinated benzylsulfones have also been developed.

  9. 動的速度論的分割を基盤とする新規不斉クロスカップリング反応の開拓

    2017.4 - 2020.3

    日本学術振興会  若手研究B 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  10. 多置換メタン類の短工程合成を指向した触媒的炭素-スルホニル結合活性化反応の開発

    2016.4 - 2018.3

    有機合成化学協会  研究企画賞 (中外製薬) 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  11. アセトニトリル誘導体への逐次的アリール化を基軸とする多置換アリールアルカン類の自在構築法の開発

    2016.4 - 2017.3

    伊藤忠兵衛基金  研究助成金 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  12. 炭素–水素結合の化学変換のみを基軸とする逐次的アリール化反応の開発と生物活性化合物創製への展開

    2014.10 - 2015.9

    服部報公会  工学研究奨励援助金 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  13. N-heterocyclic carbene-modified gold nanoparticles for biosensing

    Grant number:26288023  2014.4 - 2018.3

    Crudden Cathleen

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    Authorship:Collaborating Investigator(s) (not designated on Grant-in-Aid) 

    The goal of this grant was to prepare and test stable gold nanoparticles for potential biosensing applications. We have prepared new gold nanoparticles that were protected by carboxylate-functionalized N-heterocyclic carbenes (NHCs) to be water-souble. The resulting gold particles were stable in the presence of electrolytes and gave photoacoustic signals. In addition, we successfully increased stability of gold nanoparticles against thiols by employing bidentate NHC ligands functionalized with long alkyl chains.

  14. Modular Synthesis of Arylalkanes Using Organosulfur Compounds

    Grant number:26810056  2014.4 - 2017.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (B)

    Nambo Masakazu, CRUDDEN Cathleen M.

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    Authorship:Principal investigator 

    Grant amount:\3900000 ( Direct Cost: \3000000 、 Indirect Cost:\900000 )

    We have developed methyl sulfone derivatives as new reacting templates in Pd-catalyzed sequential arylations directed toward the modular synthesis of multiply-arylated methanes. This method enabled the rapid synthesis of thyroid hormone receptor b-selective analog (GC-24) and the development of new inhibitor for plant cell division.

  15. 有機硫黄化合物をテンプレートとするアリールアルカン類の効率的合成法の開発

    2014.4 - 2016.3

    科学研究費補助金  若手研究(B)

    南保 正和

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    Authorship:Principal investigator 

    本研究では、生物活性化合物に頻繁にみられる多置換アリールアルカン化合物群の効率的な合成手法の確立を目的とする。具体的には、スルホニル基の有する電子求引基および脱離基としての潜在的な特性に着目し、逐次的な置換基導入を可能にする新規テンプレート分子の開発と新触媒の開発を行う。また開発した手法を不斉反応へと展開し、エナンチオ選択的な多置換アリールアルカン類の合成を目指す。さらに抗癌剤や甲状腺ホルモンなどの生物活性を有する多置換アリールアルカン類の最短工程かつ実用的な合成を達成する。

  16. 有機硫黄化合物をテンプレートとするアリールアルカン類の効率的合成法の開発

    2014.4 - 2016.3

    日本学術振興会  科学研究費助成事業 若手研究B  若手研究(B)

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

    本研究では、生物活性化合物に頻繁にみられる多置換アリールアルカン化合物群の効率的な合成手法の確立を目的とする。具体的には、スルホニル基の有する電子求引基および脱離基としての潜在的な特性に着目し、逐次的な置換基導入を可能にする新規テンプレート分子の開発と新触媒の開発を行う。また開発した手法を不斉反応へと展開し、エナンチオ選択的な多置換アリールアルカン類の合成を目指す。さらに抗癌剤や甲状腺ホルモンなどの生物活性を有する多置換アリールアルカン類の最短工程かつ実用的な合成を達成する。

  17. 酸性sp3炭素-水素結合に立脚したアリールメタン類の新規合成法の開発

    Grant number:25888007  2013.8 - 2015.3

    科学研究費助成事業  研究活動スタート支援

    南保 正和

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    Authorship:Principal investigator 

    Grant amount:\2730000 ( Direct Cost: \2100000 、 Indirect Cost:\630000 )

    sp3炭素上にアリール基を有するメタン類、すなわちアリールメタン類は多くの有機材料や医農薬化合物を構成する基本骨格の1つである。本研究ではアリールメタン化合物群の短工程かつ一般的合成手法の確立を目的とし、電子求引基に置換されたメタン化合物の有する酸性sp3炭素-水素(C-H)結合のC-Hアリール化を可能にする新触媒の開発を行った。その結果、メチルフェニルスルホンと芳香族ハロゲン化物とのC-Hアリール化がパラジウム触媒存在下で進行し、アリール基が1つ、2つ導入された化合物群を選択的に合成できることを見出した。本研究の最終目標であった3つ目のアリール基導入には至らなかったが、パラジウム触媒を用いた有機ホウ素化合物との炭素-スルホン結合の切断を伴ったアリール基導入反応を新たに見出し、トリアリールメタンを得ることに成功した。反応に用いる芳香族ハロゲン化物と有機ホウ素化合物を変えることで、様々な非対称トリアリールメタンが合成可能であった。本手法を駆使することで抗乳癌活性を有する化合物の短工程での合成にも成功した。本手法で用いている基質や触媒は入手・調製容易なものであり、かつ大気下で取り扱えることも有用な点と言える。現在本手法で合成した化合物を用いて、生物活性評価を共同研究により進めている。また本研究を通じ、パラジウム触媒が通常安定な炭素-スルホン結合の切断を促進するという新しい知見を得ることができた。今後、本知見を基に新たな分子変換反応の開発にも展開する予定である。
    翌年度、交付申請を辞退するため、記入しない。
    翌年度、交付申請を辞退するため、記入しない。

  18. 多置換アリールメタン類の迅速構築法の開発と生物活性化合物合成への展開

    2013.8 - 2014.7

    日揮・実吉奨学会  研究助成金 

    南保 正和

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    Authorship:Principal investigator  Grant type:Competitive

  19. 酸性sp3炭素-水素結合に立脚したアリールメタン類の新規合成法の開発

    2013.8 - 2014.3

    科学研究費補助金 

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    Authorship:Principal investigator 

    本研究では、生物活性化合物に頻繁にみられるアリールメタン化合物群の一般的合成手法の確立 を目的とする。具体的には、電子求引基に置換されたメタン化合物の有する酸性 sp3 炭素̶水素 (C–H)結合に着目し、芳香族ハロゲン化物との C–H アリール化を可能にする新触媒の開発を行う。 さらに開発した手法を連続的な芳香環導入反応へと展開するとともに、甲状腺ホルモンや抗癌剤 として注目されている多置換アリールメタン骨格を有する化合物群の最短工程かつ効率的な合成 を達成する。

  20. 酸性sp3炭素-水素結合に立脚したアリールメタン類の新規合成法の開発

    2013.8 - 2014.3

    日本学術振興会  科学研究費助成事業 スタートアップ支援  若手研究(スタートアップ)

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    Grant type:Competitive

    本研究では、生物活性化合物に頻繁にみられるアリールメタン化合物群の一般的合成手法の確立 を目的とする。具体的には、電子求引基に置換されたメタン化合物の有する酸性 sp3 炭素̶水素 (C–H)結合に着目し、芳香族ハロゲン化物との C–H アリール化を可能にする新触媒の開発を行う。 さらに開発した手法を連続的な芳香環導入反応へと展開するとともに、甲状腺ホルモンや抗癌剤 として注目されている多置換アリールメタン骨格を有する化合物群の最短工程かつ効率的な合成 を達成する。

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Industrial property rights 5

  1. フラーレンの誘導体及びその製造方法

    伊丹健一郎, 南保正和

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    Application no:2009-202034  Date applied:2009.9

    Announcement no:2011-051930 

    Country of applicant:Domestic  

  2. フラーレンの誘導体及びその製造方法

    伊丹健一郎, 南保正和

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    Application no:2009-202034  Date applied:2009.9

    Announcement no:2011-051930 

  3. トリ(ヘテロ)アリールアセトニトリルの製造方法

    南保正和, Muhammad Yar, Cathleen M. Crudden

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    Application no:特願PCT/JP2015/84181 

  4. 植物細胞分裂抑制剤

    植田美那子, 南保正和, 栗原大輔, 桑田啓子, 大川妙子

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    Application no:特願2016-028537 

  5. トリアリールメタンの製造方法

    南保 正和, Cathleen M. Crudden

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    Application no:特願PCT/JP2014/078653 

 

Teaching Experience (Off-campus) 2

  1. 理科研究BII

    Aichi University of Education)

  2. 有機化学A

    Aichi University of Education)

 

Academic Activities 1

  1. Scientific Advisory Board, ChemRxiv

    Role(s):Review, evaluation

    2021.6

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    Type:Scientific advice/Review