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MATSUMOTO Kouichi

    Department of Science　Associate Professor
Last Updated :2024/04/25

Researcher Information

Degree

  • Doctor of Engineering（2010/03 Kyoto University）

Research Interests

  • 有機合成化学、有機反応開発、有機電解合成   

Research Areas

  • Nanotechnology/Materials / Synthetic organic chemistry
  • Other / Other
  • Nanotechnology/Materials / Structural/physical organic chemistry

Academic & Professional Experience

  • 2019/04 - Today  Kindai UniversityFaculty of Science and Engineering准教授、PI
  • 2015/04 - Today  同志社大学生命医科学部・嘱託講師（非常勤講師、春学期担当）
  • 2014/04 - 2019/03  Kindai UniversityFaculty of Science and Engineering講師（柏村成史 教授）
  • 2010/04 - 2014/03  Kindai University理工学部理学科化学コース助教（柏村成史 教授）
  • 2011/04 - 2011/09  鳥取大学工学部・非常勤講師
  • 2007/04 - 2010/03  日本学術振興会特別研究員DC1（京都大学）

Education

  • 2007/04 - 2010/04  京都大学大学院工学研究科合成・生物化学専攻博士後期課程 修了（吉田潤一 教授）
  • 2009/04 - 2009/06  ミュンヘン大学化学科（ドイツ）短期留学（Hendrik Zipse教授）
  • 2005/04 - 2007/03  京都大学大学院工学研究科合成・生物化学専攻修士課程 修了（吉田 潤一 教授）
  • 2001/04 - 2005/03  京都大学工学部工業化学科 卒業（吉田 潤一 教授）
  • 1998/04 - 2001/03  帝塚山高等学校（奈良） 卒業
  • 1995/04 - 1998/03  帝塚山中学校（奈良） 卒業

Association Memberships

  • 化学フロンティア研究会 / Chemical Frontier Workshop   公益社団法人電気化学会   公益社団法人日本化学会   

Published Papers

  • Short steps synthesis of unsymmetrical acetylenes from tetrachloroethylene and arylboronic acids using Suzuki coupling reaction and improvement of mild dechlorinations
    H. Suzuki.; A. Togo.; J. Kikuzawa.; K. Miyamoto.; S. Marumoto.; A. Kuwabara.; M. Kobayashi.; K. Matsumoto
    Chem. Lett. accepted 2024 [Refereed]
  • Concise Synthetic Routes for Diphenylacetylene from Tetrachloroethylene Using Suzuki Coupling Reaction Followed by Treatment with n-Butyllithium
    Y. Fujiki.; H. Suzuki.; J. Kikuzawa.; K. Nishiwaki.; N. Kawashita.; J. Matsuoka.; A. Nakamura; T. Maegawa.; A. Kuwabara.; M. Kobayashi.; K. Matsumoto
    Chem. Lett. accepted 2024 [Refereed]
  • Electrochemical Transformations of Carbohydrates
    Kouichi Matsumoto, Toshiki Nokami
    Current Opinion in Electrochemistry 44 101457  2024 [Refereed][Invited]
  • Electro-Generated Base from Amide Derivative Enables Cyclopropanation of Alkyl 2-Chloroacetate without Formation of Trialkyl Propane-1,2,3-carboxylate
    Kouichi Matsumoto, Mizuki Matsuse, Kengo Hamasaki, Hiyono Suzuki, Sora Okubo, Akane Togo, Yuuki Okayama, Norihito Kawashita
    Chem. Lett. in press. 2024 [Refereed]
  • Primary Amine Discrimination Using a 19F NMR Reporter Bearing two Different Fluorine-Containing Moieties
    Naoto Hamaguchi, Rina Nishizawa, Mayu Ikeda, Miki Yokoyama, Hiyono Suzuki, Kouichi Matsumoto, Tetsuo Ohta, Yohei Oe
    ChemistrySelect 9 e202303190  2024 [Refereed]
  • Kouichi Matsumoto; Yuta Hayashi; Kengo Hamasaki; Mizuki Matsuse; Hiyono Suzuki; Keiji Nishiwaki; Norihito Kawashita
    Beilstein J. Org. Chem. Beilstein Institut 18 1116 - 1122 2022/08 [Refereed][Invited]
     
    The electrochemical reduction conditions of the reaction of alkyl 2-chloroacetates in Bu4NBr/DMF using a divided cell equipped with Pt electrodes to produce the corresponding cyclopropane derivatives in moderate yields were discovered. The reaction conditions were optimized, the scope and limitations, as well as scale-up reactions were investigated. The presented method for the electrochemical production of cyclopropane derivatives is an environmentally friendly and easy to perform synthetic procedure.
  • Kouichi Matsumoto; Kazuhiro Yamashita; Yuuki Sakoda; Hinata Ezoe; Yuki Tanaka; Tatsuya Okazaki; Misaki Ohkita; Senku Tanaka; Yuki Aoki; Daisuke Kiriya; Shigenori Kashimura; Masahiko Maekawa; Takayoshi Kuroda-Sowa; Takashi Okubo
    Eur. J. Org. Chem. WILEY-V C H VERLAG GMBH 2021 (33) 4620 - 4629 1434-193X 2021/09 [Refereed]
     
    New star-shaped non-fullerene acceptors (5Z,5 ' Z,5 '' Z)-5,5 ',5 ''-((benzo[1,2-b : 3,4-b ' : 5,6-b '']trithiophene-2,5,8-triyltris(4-octylthiophene-5,2-diyl))tris(methaneylylidene))tris(3-octyl-2-thioxothiazolidin-4-one) (1: BTT-OT-ORD) and 2,2 ',2 ''-((5Z,5 ' Z,5 '' Z)-((benzo[1,2-b : 3,4-b ' : 5,6-b '']trithiophene-2,5,8-triyltris(4-octylthiophene-5,2-diyl))tris(methaneylylidene))tris(3-octyl-4-oxothiazolidine-5,2-diylidene))trimalononitrile (2: BTT-OT-OTZDM) with a benzotrithiophene core, alkyl-thiophen units, and acceptor units were designed and synthesized. The HOMO-LUMO levels of 1 and 2 were determined by photoemission spectroscopy and UV-Vis absorption spectroscopy. Binary blend and ternary blend bulk heterojunction (BHJ) organic solar cells with non-fullerene acceptors 1 and 2 were fabricated with the inverted device structures of glass/ITO/ZnO/active_layer/MoO3/Ag. Both binary blend BHJ solar cells with 1 and 2 show lower J(SC) and larger V-OC values than P3HT : PCBM solar cells. On the other hand, ternary blend BHJ organic solar cells, including 10 % of 1, exhibited a larger power conversion efficiency than P3HT : PCBM solar cells because the J(SC) value was largely improved.
  • One-Pot Synthetic Approaches for the Construction of Isochroman-4-ones and Benzoxazin-3-ones Using O,P-Acetals
    Akira Nakamura, Kouhei Yamamoto, Ryo Murakami , Norihito Kawashita, Kouichi Matsumoto, Tomohiro Maegawa
    Synthesis 53 (20) 3862 - 3868 2021 [Refereed]
  • Kouichi Matsumoto, Masahiro Matsumoto, Terumasa Hayashi, Masahiko Maekawa, Keiji Nishiwaki, Shigenori Kashimura
    Electrochemistry The Electrochemical Society of Japan 88 (4) 314 - 320 1344-3542 2020/07 [Refereed]
     

    The electrochemical reduction of anthracenes in the presence of esters and chlorotrimethylsilane in LiClO4/THF in the undivided cell equipped with magnesium electrodes affords the corresponding cyclized products at low to moderate yields. Herein, the chemical structure of the product is determined by X-ray analysis, as well as 1H NMR, 13C NMR, and HRMS. The in situ generation of magnesium anthracenes is indicated. The scope and limitations of the current reactions using anthracene and its derivatives with various esters are investigated.

  • Improved and Practical Synthesis of the Integrastatin Core
    Yoshiro Yamagiwa, Nozomi Haruna, Hideki Kawakami, Kouichi Matsumoto
    Bull. Chem. Soc. Jpn. 93 (8) 1036 - 1042 2020 [Refereed]
  • Kouichi Matsumoto; Hiroki Shimao; Yuta Fujiki; Norihito Kawashita; Shigenori Kashimura
    Electrochemistry The Electrochemical Society of Japan 88 (4) 262 - 264 1344-3542 2020 [Refereed]
  • Synthesis of Oxazolines from N-Allylamides Using an Electrochemically Generated Ars(ArSSAr)+ Pool
    Yu Miyamoto; Naoya Mitani; Rina Yanagi; Shigenori Kashimura; Seiji Suga; Jun-ichi Yoshida; Kouichi Matsumoto
    Heterocycles 96 (8) 1373 - 1382 2018 [Refereed]
  • Kouichi Matsumoto; Rina Yanagi; Kouji Yamaguchi; Erin Hayashi; Eri Yasuda; Toshiki Nokami; Keiji Nishiwaki; Shigenori Kashimura; Kaho Kuriyama
    Heterocycles The Japan Institute of Heterocyclic Chemistry 96 (8) 1363 - 1372 0385-5414 2018 [Refereed]
  • Akihiro Shimizu; Shun Horiuchi; Ryutaro Hayashi; Kouichi Matsumoto; Yu Miyamoto; Yusuke Morisawa; Tomonari Wakabayashi; Jun-ichi Yoshida
    Arkivoc ARKAT USA INC 2018 (part ii) 97 - 113 1551-7004 2018 [Refereed][Invited]
     
    Thiirenium ions generated and accumulated by low-temperature electrochemical oxidation of disulfides in the presence of alkynes were successfully observed by low-temperature NMR, Raman, and mass spectroscopies and were found to be stable at temperatures below -40 degrees C. The thiirenium ions showed ambident reactivity toward subsequently added nucleophiles to give either disubstituted alkenes or alkynes depending on the nature of the nucleophiles.
  • 義富卓也; 高田謙; 谷合伯斗; 安東秀峰; 松本浩一; 田中仙君
    電気学会論文誌 C 138 (11) 1298 - 1304 0385-4221 2018 [Refereed]
  • Electrochemical Methods as Enabling Tools for Glycosylation
    Manmode, Sujit; Matsumoto, Kouichi; Nokami, Toshiki; Itoh, Toshiyuki
    Asian J. Org. Chem. 7 (9) 1719 - 1729 2018 [Refereed]
  • 「電解発生中間体のスペクトル測定」（和文）
    菅 誠治,光藤耕一,野上敏材,松本浩一
    電気化学および工業物理化学 85 (11) 754 - 758 2017/11 [Refereed][Invited]
  • Hideo Ando; Senku Tanaka; Kouichi Matsumoto; Yoshihide Nakao
    Chem. Phy. Lett. ELSEVIER SCIENCE BV 687 60 - 65 0009-2614 2017/11 [Refereed]
     
    In poly(3-hexylthiophene) (P3HT), it is suggested that bromination disturbs the pi conjugation and reduces the carrier mobility. To investigate the deconjugation mechanism, we theoretically studied a key flexibility of the Br-P3HT backbone, namely inter-ring S-C-C-S dihedral torsion, in terms of potential energy curve, geometry-based aromaticity index, and decomposed energies of inter-monomer interaction. The linkage between bromination and the excitation energy was also investigated. We concluded that steric repulsion due to bulky bromo group can cause out-of-plane S-C-C-S torsion of Br-P3HT and consequent shortening of the conjugation length, not electronic substituent effect, leads to blue shift of the S-0 -> S-1 excitation energy. (C) 2017 Elsevier B.V. All rights reserved.
  • Senku Tanaka; Siti Khadijah Binti Rosli; Ken Takada; Norito Taniai; Takuya Yoshitomi; Hideo Ando; Kouichi Matsumoto
    RSC Advances ROYAL SOC CHEMISTRY 7 (74) 46874 - 46880 2046-2069 2017 [Refereed]
     
    We examined the effects of delocalized pi-electrons in poly(3-hexylthiophene) (P3HT) on the photovoltaic properties of a bulk heterojunction (BHJ) solar cell. The pi-conjugated length of P3HT was controlled by modification of P3HT through partial bromination at the 4-position of thiophene units. We investigated correlation between the degree of P3HT bromination (2, 11, 22, 37, 66, 84, 100%) and the photovoltaic properties of Br-P3HT:phenyl-C-61-butyric acid methyl ester (PCBM) BHJ solar cells. The power conversion efficiency of the 11% Br-P3HT:PCBM solar cell decreased to 56% of that of a pristine P3HT:PCBM solar cell. The main factor contributing to this decrease was lower short circuit currents. The photo absorption spectrum and the X-ray diffraction pattern of the 11% Br-P3HT film showed only slight differences to those of pristine P3HT, indicating the interchain pi-stacking of the polymers was almost unaffected by the 11% bromination. These results suggest that an intrachain pi-conjugation across more than 10 thiophene rings in the P3HT backbone is necessary to realize efficient charge transport in polymer domains. The 37% Br-P3HT:PCBM cell showed only weak photovoltaic properties; both inter- and intrachain delocalization of pi-electrons were disturbed by bromination.
  • Miyamoto Yu; Yamada Yuki; Shimazaki Hayato; Shimada Kazuaki; Nokami Toshiki; Nishiwaki Keiji; Kashimufta Shigenori; Matsumoto Kouichi
    Electrochemistry 83 (3) 161 - 164 1344-3542 2015/03 [Refereed]
  • Kouichi Matsumoto; Yu Miyamoto; Kazuaki Shimada; Yusuke Morisawa; Hendrik Zipse; Seiji Suga; Jun-ichi Yoshida; Shigenori Kashimura; Tomonari Wakabayashi
    Chem. Commun. ROYAL SOC CHEMISTRY 51 (66) 13106 - 13109 1359-7345 2015 [Refereed]
  • Kouichi Matsumoto; Hayato Shimazaki; Yu Miyamoto; Kazuaki Shimada; Fumi Haga; Yuki Yamada; Hirotsugu Miyazawa; Keiji Nishiwaki; Shigenori Kashimura
    J. Oleo Sci. JAPAN OIL CHEMISTS SOC 63 (5) 539 - 544 1345-8957 2014/05 [Refereed]
     
    A simple and convenient method has been developed for the synthesis of esters from the corresponding carboxylic acids and alkyl halides by using a stoichiometric amount of tetrabutylammonium fluoride (Bu4NF) as the base. The reaction of carboxylic acids and a Bu4NF/THF solution in DMF or THF as the solvent generates carboxylate ions in situ. The carboxylate ions thus generated and accumulated are highly reactive. They are then allowed to react with alkyl halides as the electrophiles, and afford the corresponding esters in moderate to good yields. The reaction without Bu4NF does not afford any product; therefore, Bu4NF seems to play an important role as the base in these reactions. A bulky countercation such as the tetrabutylammonium cation seems to increase the reactivity of the carboxylate ions in the solution phase.
  • Jun-Ichi Yoshida; Yosuke Ashikari; Kouichi Matsumoto; Toshiki Nokami
    J. Syn. Org. Chem. Jpn./Yuki Gosei Kagaku Kyokaishi 71 (11) 1136 - 1144 0037-9980 2013/11 [Refereed][Invited]
     
    The "cation pool" method involves the generation and accumulation of highly reactive organic cations in solution. These can serve as powerful carbon and heteroatom electrophiles in organic synthesis. Recent developments in the cation pool method including the indirect cation pool method, cation chain reactions, and integrated electrochemical-chemical reactions are described.
  • ’Electrogenerated Acid (EGA) catalyzed Addition of Diaryldisulfides to Carbon-Carbon Multiple Bonds
    Kouichi Matsumoto, Hayato Shimazaki, Tomonari Sanada, Kazuaki Shimada, Shino Hagiwara, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida
    Chem. Lett. 42 (8) 843 - 845 2013 [Refereed]
  • The Addition of ArSSAr to Alkenes. Implication of the Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)+
    Kouichi Matsumoto, Tomonari Sanada, Hayato Shimazaki, Kazuaki Shimada, Shino Hagiwara, Shunsuke Fujie, Yosuke Ashikari, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida
    Asian J. Org. Chem. 2 (4) 325 - 329 2013 [Refereed]
  • Kouichi Matsumoto; Yuki Kozuki; Yosuke Ashikari; Seiji Suga; Shigenori Kashimura; Jun-ichi Yoshida
    Tetrahedron Lett. PERGAMON-ELSEVIER SCIENCE LTD 53 (15) 1916 - 1919 0040-4039 2012 [Refereed]
     
    Arylbis(arylthio)sulfonium ions (ArS(ArSSAr)(+)), which were generated and accumulated by the low-temperature electrolysis of diary! disulfide (ArSSAr), were found to serve as ArS+ equivalent in electrophilic substitution reactions of aromatic compounds, enolizable ketones, enol acetates, ketene silyl acetals and allylsilanes to give the corresponding arylthiolated products. (C) 2012 Elsevier Ltd. All rights reserved.
  • Kouichi Matsumoto; Seiji Suga; Jun-ichi Yoshida
    Org. Biomol. Chem. ROYAL SOC CHEMISTRY 9 (8) 2586 - 2596 1477-0520 2011 [Refereed]
     
    Low-temperature electrochemical oxidation of ArSSAr was carried out to generate a pool of "ArS+". Spectroscopic studies (H-1 NMR and CSI-MS) of the resulting solution revealed the accumulation of ArS(ArSSAr)(+). The resulting "ArS+" pool reacted with alkenes and alkynes to give diarylthio-substituted products. The "ArS+" pool rapidly reacted with thioacetals to give the corresponding alkoxycarbenium ion pools, which reacted with various carbon nucleophiles (indirect cation pool method). The reaction of the alkoxycarbenium ion pools with stilbene derivatives in the presence of ArSSAr gave thiochroman derivatives. In addition to such stoichiometric reactions, a catalytic amount of "ArS+" serves as an initiator and a chain carrier of some cationic chain reactions involving intramolecular carbon-carbon bond formation. In situ generation of "ArS+" by electrochemical oxidation of ArSSAr with a catalytic amount of electricity in the presence of a substrate is also effective for such cationic chain reactions.
  • Kodai Saito; Koji Ueoka; Kouichi Matsumoto; Seiji Suga; Toshiki Nokami; Jun-ichi Yoshida
    Angew. Chem., Int. Ed. WILEY-V C H VERLAG GMBH 50 (22) 5153 - 5156 1433-7851 2011 [Refereed]
  • Shunsuke Fujie; Kouichi Matsumoto; Seiji Suga; Toshiki Nokami; Jun-ichi Yoshida
    Tetrahedron PERGAMON-ELSEVIER SCIENCE LTD 66 (15) 2823 - 2829 0040-4020 2010/04 [Refereed]
     
    ArS(ArSSAr)(+) (arylbis(arylthio)sulfonium ions), which were generated and accumulated by the electro-chemical oxidation of diaryl disulfides (ArSSAr) in CH(2)Cl(2) at -78 degrees C, reacted with alkenes to give the corresponding diarylthio-substituted compounds in a stereospecific manner in good yields, when the reaction was quenched with a soft nucleophile, such as allylsilanes, ketene silyl acetals, and triethylamine. A mechanism involving the initial formation of an episulfonium ion followed by ring-opening by the attack of ArSSAr has been suggested. The reactions of ArS(ArSSAr)(+) with alkynes also took place to give 1,2-diorganothio-substitued alkenes stereoselectively under similar conditions. (C) 2010 Published by Elsevier Ltd.
  • Kouichi Matsumoto; Koji Ueoka; Shinkiti Suzuki; Seiji Suga; Jun ichi Yoshida
    Tetrahedron PERGAMON-ELSEVIER SCIENCE LTD 65 (52) 10901 - 10907 0040-4020 2009/12 [Refereed]
     
    Thioacetals were found to be effective precursors to generate and accumulate alkoxycarbenium ions based on direct and indirect cation pool methods. Alkoxycarbenium ions thus generated reacted with carbon nucleophiles such as allylsilanes and enol silyl ethers to give C-C bond formation products in good yields. © 2009 Elsevier Ltd. All rights reserved.
  • Shunsuke Fujie; Kouichi Matsumoto; Seiji Suga; Jun-ichi Yoshida
    Chem. Lett. CHEMICAL SOC JAPAN 38 (12) 1186 - 1187 0366-7022 2009/12 [Refereed]
     
    The reaction of alkenes and alkynes with ArS(ArSSAr)(+)BF4-, which was generated and accumulated by the low-temperature anodic oxidation of ArSSAr in Bu4NBF4/CH2Cl2, led to the addition of an ArS group and fluoride across the carbon-carbon multiple bond to give thio-fluorinated compounds in good yields.
  • Kouichi Matsumoto, Shunsuke Fujie, Seiji Suga, Toshiki Nokami, Jun-ichi Yoshida
    Chem. Commun. (36) 5448 - 5450 1359-7345 2009 [Refereed]
     
    A catalytic amount of electrochemically generated "ArS +" ("ArS+" = ArS(ArSSAr)+) initiates a cation chain reaction of dienes that involves the addition of ArSSAr associated with stereoselective intramolecular carbon-carbon bond formation, and the direct (in-cell) electrolysis of a mixture of a diene and ArSSAr with a catalytic amount of electricity also effectively initiates the reaction. © The Royal Society of Chemistry 2009.
  • Kouichi Matsumoto; Koji Ueoka; Shunsuke Fujie; Seiji Suga; Jun ichi Yoshida
    Heterocycles PERGAMON-ELSEVIER SCIENCE LTD 76 (2) 1103 - 1119 0385-5414 2008/11 [Refereed][Invited]
     
    A method for the synthesis of thiochromans based on the reactions of stilbenes and alkoxycarbenium ion pools, which were generated and accumulated by the reaction of anodically generated ArS(ArSSAr)+ with thioacetals, has been developed. © 2008 The Japan Institute of Heterocyclic Chemistry All rights reserved.
  • Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun-ichi Yoshida
    Angew. Chem., Int. Ed. WILEY-V C H VERLAG GMBH 47 (13) 2506 - 2508 1433-7851 2008 [Refereed]
     
    (Figure Presented) The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr)-+B(C6F5) 4-, or the electrolysis of a mixture of an olefinic thioacetal and ArSSAr, gives rise to effective intramolecular carbon-carbon bond formation (see scheme). This transformation opens up great potential for electroinitiated cation chain reactions in organic synthesis. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
  • Seiji Suga, Kouichi Matsumoto, Koji Ueoka, Jun-ichi Yoshida
    J. Am. Chem. Soc. AMER CHEMICAL SOC 128 (24) 7710 - 7711 0002-7863 2006 [Refereed]
     
    A sequential one-pot indirect cation pool method has been developed. The method involves the electrochemical generation and accumulation of ArS(ArSSAr)+ at low temperature (step 1) and the follow-up reaction with a thioacetal to generate an alkoxycarbenium ion pool (step 2), which reacts with various carbon nucleophiles (step 3). Steps 2 and 3 are extremely fast. The electrogenerated ArS(ArSSAr)+ was well-characterized by 1H NMR and CSI-MS. The alkoxycarbenium ion pool generated by the present indirect method exhibited 1H and 13C NMR spectra and thermal stability similar to those of the alkoxycarbenium ion pool generated by the direct electrochemical method. Copyright © 2006 American Chemical Society.
  • Generation of Alkoxycarbenium Ion Pools from Thioacetals and Applications to Glycosylation Chemistry
    Shinkiti Suzuki, Kouichi Matsumoto, Kohsuke Kawamura, Seiji Suga, Jun-ichi Yoshida
    Org. Lett. 6 (21) 3755 - 3758 2004 [Refereed]

Books etc

  • 第7章「電解発生活性種を利用する有機電解合成」淵上・跡部・稲木編著「有機電解合成の新潮流」
    松本浩一; 若林知成 シーエムシー出版 2021/11
  • ''Paired Electrolysis'' in Organic Redox Chemistry, Yoshida, J.; Patureau, F. W. Eds.
    Matsumoto, K; Nokami, T Wiley 2021
  • (Chapter 2) ’’Recent advances in the synthesis of carboxylic acid esters’’ in Carboxylic Acid - Key Role in Life Sciences (Book Title)
    Kouichi Matsumoto; Rina Yanagi; Yohei Oe InTechOpen社 2018/06
  • 28章8節 電解発生酸・塩基を用いる有機電解合成」有機合成化学実験法ハンドブック第2版
    柏村成史; 松本浩一 公益財団法人有機合成化学協会編，丸善 2015/11
  • ’’Electrogenerated Base’’ in Encyclopedia of Applied Electrochemistry
    Shigenori Kashimura; Kouichi Matsumoto Springer社 2014/04
  • 反応から学ぼう有機化学の基礎
    柏村成史; 山際由朗; 末永勇作; 佐賀佳央; 松本浩一 2010/11

MISC

Industrial Property Rights

  • 特願2024-18296:「タイトル非公開」  2024年/02/09
    松本浩一、他  学校法人近畿大学、他
  • 特許7418768(国内権利化済み):METHOD FOR PRODUCING DIARYLACETYLENE DERIVATIVE  
    MATSUMOTO, Kouichi, Other  Kinki University, Other
  • 特願2024-002858:「タイトル非公開」  2024年/01/11
    松本浩一、他  学校法人近畿大学、他
  • 特願2024-002873:「タイトル非公開」  2024年/01/11
    松本浩一、他  Kindai University
  • 特願2023-197997:「タイトル非公開」  2023年/11/22
    松本浩一、他  Kinki University, Others
  • 特許7194404:（国内権利化済み）Ｄ－ルシフェリン及びＤ－ルシフェリン誘導体、並びにこれら化合物の前駆体、並びにこれらの製造方法  
    松本浩一、他  Kinki University, Other

Awards & Honors

  • 2022/11 公益社団法人有機合成化学協会・関西支部 2022年度 有機合成化学協会関西支部賞 （第20回）
  • 2022/09 公益社団法人日本工学教育協会 第26回（2021年度）工学教育賞「奨励部門」
  • 2020 公益社団法人電気化学会有機電子移動化学研究会 2020年度 有機電子移動化学奨励賞
  • 2012 一般財団法人総合研究奨励会 2011年度 総合研究奨励賞
  • 2009 公益社団法人日本化学会 2009年度 第89春季年会・学生講演賞

Research Grants & Projects

  • 低環境負荷とハイスループットを指向した有機電解合成による新規反応開拓と装置開発
    Date (from‐to) : 2024/04 -2027/03 
    Author : 松本浩一
  • 日本学術振興会：科学研究費助成事業
    Date (from‐to) : 2020/04 -2023/03 
    Author : 松本 浩一; 安東 秀峰
     
    ① 前年度に引き続き、Hiltらの論文（Org. Lett, 2020, 22, 5968.）に基づき、エノールシリルエーテルを陽極酸化の基質として用いて、モノヨウ素化の条件検討を行った。陽極室に、LiClO4/CH3CN, NaIを溶解させて電解酸化を行うと、安定して60～70%（NMR収率）台にてモノヨウ素化体が得られる条件を確立した。またこのような検討を受け、両極合成として、陰極にチオフェノールを用いて電解合成と溶液移動を行うと、対応する硫黄置換体生成物が20%台の収率で得られることを見出した。現在、条件検討を行い、収率の向上の条件を探索している。 ② 前年度に展開を開始したイミニウムカチオンとアリルシランのin-situ合成と溶液移動による炭素－炭素結合形成は順調に進展しており、条件検討や基質（陰極）の適用範囲などの把握を行い、うまく進展している。 モデル反応では、目的生成物は60%収率（単離）で得られている。 ③ また、含イオウ化合物として、低温陽極酸化による硫黄で安定化された炭素カチオンの発生とこれを利用した両極合成についても、先行研究の論文：吉田、清水ら、Bull. Chem. Soc. Jpn. 2016, 89, 61.を参考にして、令和３年度より検討を開始している。 ④ その他、電解還元によるシクロプロパン化反応なども見出し、条件検討や適用範囲の精力的な調査を行い、その確立に成功した。 令和３年度は主に研究補助者２名とともにテーマを推進した。
  • Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research
    Date (from‐to) : 2014/04 -2017/03 
    Author : MATSUMOTO Kouichi
     
    We have develped new monitoring system in electro-oranic chemistry by Raman spectroscopy system, in which unstable organic reactive species were observed at low temperature. In addition, we have established the recycling flow system of electro-synthesis, in which in situ Raman spectroscopy was measured for kinetic analysis. Thus, we have demonstrated that Raman spectroscopy is powerful tool for reaction design, kinetic analysis, and the detection of reactive species in electro-organic chemistry.
  • 日本学術振興会：科学研究費助成事業
    Date (from‐to) : 2007 -2010 
    Author : 松本 浩一
     
    本年度は、前年度までに達成した有機反応(ArSSArの電極酸化によるArS(ArSSAr)^+の生成、および本活性種を用いたインダイレクト・カチオンプール法の開発)の反応機構の解析を詳細に行うために分子軌道計算を用いて検討した。まず、ArSSArの低温電解酸化反応により発生・蓄積した有機イオウカチオン種ArS(ArSSAr)^+の生成メカニズムを検討した。ArSSAr(Ar=p-FC_6H_4)の1電子酸化により発生すると考えられるArSSAr^+やArSなど、反応に関与すると考えられる分子、活性種について分子軌道計算により最安定構造を求めるとともに反応エネルギーを算出した。計算方法は、MP2/6-311+G(3df,2p)//mPW1K/6-31+G(2d)を採用した。その結果、ArSSArの1電子酸化により生成するArSSAr^+のS-S結合開裂のエネルギーは中性のArSSAr分子のS-S結合開裂のエネルギーよりも大きくなっており、電極上でArSSArの1電子酸化で生成したArSSAr^+のS-S結合は単独で結合開裂する可能性は低いことが示唆された。様々な反応経路を検討したところ、ArSSAr^+とArSSArが反応することでArS(ArSSAr)^+が生成する経路(ArSSAr^++ArSSAr→ArS(ArSSAr)^++1/2ArSSAr)は20.0kcal/molの発熱反応であり、エネルギー的に最も有利な経路であることを明らかにした。このように、ArSSArの電解酸化で生じるArSSAr^+種のS-S結合は単独で結合開裂しているのではなく、もう一分子のArSSArにより、それが促進されていることが明らかになった。現在、ArS(ArSSAr)^+が生成する経路がおおよそに分かってきたので、本カチオン種生成に関する遷移状態を求めるためにさらなる検討をしている段階であるとともに、インダイレクト・カチオンプール法によるアルコキシカルベニウムイオン生成に関しても、分子軌道計算によりその解析を検討している。

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    Date : 2024/04/12
    Program, newspaper magazine: 読売新聞 科学・医療欄、朝刊
  • 「近畿大と日本理化学工業、ホタル発光物質を2工程で安価に合成」
    Date : 2024/03/26
    Publisher, broadcasting station: 日刊工業新聞
  • 「試薬等に用いられるホタルルシフェリンの画期的な合成方法を開発 今後より安価で迅速な製造工程の確立に期待」
    Date : 2024/03/13
    Publisher, broadcasting station: NEWSCST（近畿大学からのプレスリリース）
    https://newscast.jp/news/3175132 Internet

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