Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Highly selective Ir-catalyzed direct sixfold borylation of peripheral aromatic substituents on hexakisaryl-substituted [28]hexaphyrin(1.1.1.1.1.1) Reviewed International journal

Goro Mori, Hiroshi Shinokubo, Atsuhiro Osuka

TETRAHEDRON LETTERS Vol. 49 ( 13 ) page： 2170 - 2172 2008.3

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

Direct functionalization of aromatic substituents on [28]hexaphyrin was achieved by Ir-catalyzed borylation with the Smith-Miyaura-Hartwig protocol. High para. selectivity was observed in the reaction on 2,6-dichlorophenyl and 2,6-dimethoxyphenyl substituents of [28]hexaphyrin. The reaction with [26]hexaphyrin resulted only in reduction of the substrate to provide [28]hexaphyrin without borylation, thus highlighting the importance of the oxidation state of substrates in this catalytic transformation. The borylated hexaphyrin can be used for Suzuki-Miyaura cross-coupling reaction. (c) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2008.01.069

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Highly selective Ir-catalyzed direct sixfold borylation of peripheral aromatic substituents on hexakisaryl-substituted [28]hexaphyrin(1.1.1.1.1.1) Reviewed International journal

Mori Goro, Shinokubo Hiroshi, Osuka Atsuhiro

Tetrahedron Letters Vol. 49 ( 13 ) page： 2170 - 2172 2008.3

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

Direct functionalization of aromatic substituents on [28]hexaphyrin was achieved by iridium-catalyzed borylation with theSmith–Miyaura–Hartwig protocol. High para selectivity was observed in the reaction on 2,6-dichlorophenyl and 2,6-dimethoxyphenylsubstituents of [28]hexaphyrin. The reaction with [26]hexaphyrin resulted only in reduction of the substrate to provide [28]hexaphyrinwithout borylation, thus highlighting the importance of the oxidation state of substrates in this catalytic transformation. The borylatedhexaphyrin can be used for Suzuki–Miyaura cross coupling reaction.

CiNii Research

Dimeric assemblies from 1 2,3-triazole-appended Zn(II) porphyrins with control of NH-tautomerism in 1 2,3-triazole Reviewed International journal

Chihiro Maeda, Shigeru Yamaguchi, Chusaku Ikeda, Hiroshi Shinokubo, Atsuhiro Osuka

ORGANIC LETTERS Vol. 10 ( 4 ) page： 549 - 552 2008.2

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

Cu(I)-catalyzed 1,3-dipolar cycloaddition of meso-ethynyl Zn(II) porphyrin with benzyl azide efficiently provides meso-1-benzyl-1H-1,2,3-triazolyl Zn(II) porphyrin, which assembles to form a slipped cofacial dimer by the complementary coordination of the triazole nitrogen atom at the 3-position to the zinc center of a second porphyrin moiety both in the solid and solution states. Removal of the benzyl protection and introduction of a 2-ethoxycarbonylphenyl moiety greatly stabilize the dimeric assembly through an additional hydrogen bonding interaction between the NH proton of 2H-1,2,3-triazole and the carbonyl oxygen.

DOI： 10.1021/ol7028299

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meso-Aryl Substituted Rubyrin and Its Higher Homologues: Structural Characterization and Chemical Properties Reviewed

Soji Shimizu, Shohei Saito, Won-Seob Cho, Jonathan L. Sessler, Hiroshi Shinokubo, and Atsuhiro Osuka

Chem. Eur. J. Vol. 14 ( 9 ) page： 2668-2678 2008.2

Efficient Rhodium-Catalyzed installation of unsaturated ester functions onto porphyirins: Site-specific heck-type addition versus conjugate addition Reviewed International journal

Hiromi Baba, Jinping Chen, Hiroshi Shinokubo, Atsuhiro Osuka

CHEMISTRY-A EUROPEAN JOURNAL Vol. 14 ( 14 ) page： 4256 - 4262 2008

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

A facile introduction of alpha,beta-or alpha,beta,gamma,delta-unsaturated ester functions onto porphyrins was achieved through rhodium-catalyzed addition of beta-borylporphyrins to acrylate or 2,4-pentadienoate esters. The reaction of meso-borylporphyrins with acrylates exclusively afforded saturated esters by 1,4-conjugate addition under the same re-mode (Heck-type versus conjugate addition) is highly dependent on the reaction site (beta versus meso). This functionalization has a significant impact on the electronic properties of the pi system of porphyrins, which induces a substantial redshift and broadening in the absorption spectra by effective conjugation through the beta positions. The coplanar structure of the unsaturated ester moieties with respect to the porphyrin core has been unambiguously elucidated by X-ray crystallographic analysis.

DOI： 10.1002/chem.200701943

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Metalation of expanded porphyrins: A chemical trigger used to produce molecular twisting and Mobius aromaticity Reviewed International journal

Yasuo Tanaka, Shohei Saito, Shigeki Mori, Naoki Aratani, Hiroshi Shinokubo, Naoki Shibata, Yoshiki Higuchi, Zin Seok Yoon, Kil Suk Kim, Su Bum Noh, Jong Kang Park, Dongho Kim, Atsuhiro Osuka

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 47 ( 4 ) page： 681 - 684 2008

Synthesis of chiral porphyrins through Pd-catalyzed [3+2] annulation and heterochiral self-assembly Reviewed International journal

Masatoshi Mizumura, Hiroshi Shinokubo, Atsuhiro Osuka

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 47 ( 29 ) page： 5378 - 5381 2008

Unambiguous Identification of Mobius Aromaticity for meso-Aryl-Substituted [28]Hexaphyrins (1. 1. 1. 1. 1. 1) Reviewed International journal

忍久保洋

J. Am Chem. Soc. 130 page： 13568 - 13579 2008

Synthesis and Characterization of Pyridine-fused Porpyrinoid Reviewed International journal

Tokuji Sumito, Shinokubo Hiroshi, Osuka Atsuhiro

Abstracts of Symposium on Physical Organic Chemistry Vol. 2008 ( 0 ) page： 51 - 51 2008

Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Society of Physical Organic Chemistry, Japan

The introduction of fused π-conjugated segments to porphyrin is expected to create a variety of conjugated porphyrin systems that would exhibit unique optical and electrochemical properties. We have previously reported the formation of dehydropurpurin from <I>meso</I>-bromoporphyrins in the presence of palladium catalyst and its conversion into 3,5-dibenzoylporphyrin by oxidation of the outer C-C double bond. This time we have found that pyridine-fused porphyrinoid was formed by the reaction of 3,5-dibenzoylporphyrin with ammonium acetate. The framework of this compound contains pyridine and carbonyl moieties. X-Ray crystallographic analysis unambiguously elucidated its structure. Both its structure and optical property will be presented.

DOI： 10.11494/kisoyuki.2008.0.51.0

CiNii Research

Synthesis of meso-5-Azaindolyl Appended Zn(II) Porphyrins via Pd-Catalyzed Annulation Reviewed

Chihiro Maeda, Hiroshi Shinokubo, and Atsuhiro Osuka

Org. Lett. Vol. 9 ( 13 ) page： 2493-2496 2007.6

Synthesis of Doubly β-to-β 1,3-Butadiyne-Bridged Diporphyrins: Enforced Planar Structures and Large Two-photon Absorption Cross Sections Reviewed

Ichiro Hisaki, Satoru Hiroto, Kil Suk Kim, Su Bum Noh, Dongho Kim, Hiroshi Shinokubo, and Atsuhiro Osuka

Angew. Chem., Int. Ed. Vol. 46 ( 27 ) page： 5125-5128 2007.6

Regioselective Borylation of Porphyrins via C-H Bond Activation under Iridium Catalysis That Affords Useful Building Blocks for Porphyrin Assemblies Reviewed

Hiroshi Hata, Shigeru Yamaguchi, Goro Mori, Satomi Nakazono, Taisuke Katoh, Keishi Takatsu, Satoru Hiroto, Hiroshi Shinokubo, and Atsuhiro Osuka

Chem. Asian J. Vol. 2 ( 7 ) page： 849-859 2007.5

Porphyrin Pincer Complexes: Peripherally Cyclometallated Porphyrins and Their Catalytic Activities Controlled by Central Metals Reviewed

Shigeru Yamaguchi, Taisuke Katoh, Hiroshi Shinokubo, and Atsuhiro Osuka

J. Am. Chem. Soc. Vol. 129 ( 20 ) page： 6392-6393 2007.5

Facile Peripheral Functionalization of Porphyrins via Pd-Catalyzed [3 + 2] Annulation with Alkynes Reviewed

Akhila K. Sahoo, Shigeki Mori, Hiroshi Shinokubo, and Atsuhiro Osuka

Angew. Chem., Int. Ed. Vol. 45 ( 47 ) page： 7972-7975 2006.11

Synthesis and Biradicaloid Character of Doubly Linked Corrole Dimers Reviewed

Satoru Hiroto, Ko Furukawa, Hiroshi Shinokubo, and Atsuhiro Osuka

J. Am. Chem. Soc. Vol. 128 ( 38 ) page： 12380-12381 2006.9

Intermolecular Rhodium-Catalyzed Carbometallation-Heck-Type Reaction in Water Reviewed

Takuya Kurahashi, Hiroshi Shinokubo, and Atsuhiro Osuka

Angew. Chem., Int. Ed. Vol. 45 ( 38 ) page： 6336-6338 2006.8

Synthesis of Brominated Directly Fused Diporphyrins through Gold(III)-Mediated Oxidation Reviewed

Akhila K. Sahoo, Yasuyuki Nakamura, Naoki Aratani, Kil Suk Kim, Su Bum Noh, Hiroshi Shinokubo, Dongho Kim, and Atsuhiro Osuka

Org. Lett. Vol. 8 ( 18 ) page： 4141-4144 2006.8

Porphyrin Synthesis in Water Provides New Expanded Porphyrins with Direct Bipyrrole Linkages: Isolation and Characterization of Two Heptaphyrins Reviewed

Satoru Hiroto, Hiroshi Shinokubo, and Atsuhiro Osuka

J. Am. Chem. Soc. Vol. 128 ( 20 ) page： 6568-6569 2006.5

A Directly Fused Tetrameric Porphyrin Sheet and Its Anomalous Electronic Properties That Arise from the Planar Cyclooctatetraene Core Reviewed

Yasuyuki Nakamura, Naoki Aratani, Hiroshi Shinokubo, Akihiko Takagi, Tomoji Kawai, Takuya Matsumoto, Zin Seok Yoon, Deok Yun Kim, Tae Kyu Ahn, Dongho Kim, Atsuya Muranaka, Nagao Kobayashi, and Atsuhiro Osuka

J. Am. Chem. Soc. Vol. 129 ( 12 ) page： 4119-4127 2006.3

Oxidation of gem-Borylsilylalkylcoppers to Acylsilanes with Air Reviewed

Junichi Kondo, Hiroshi Shinokubo, and Koichiro Oshima

Org. Lett. Vol. 8 ( 6 ) page： 1185-1187 2006.3

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Papers - SHINOKUBO, Hiroshi