Grant-in-Aid for Scientific Research on Innovative Areas FY2017-2021Hybrid Catalysis

Tatsuhiko Yoshino » Japanese

Affiliation Faculty of Pharmaceutical Sciences, Hokkaido University
Position Lecturer
Contact Email
HP http://www.pharm.hokudai.ac.jp/yakuzou/index_e.html
Speciality Organic Synthetic Chemistry, Organometallic Chemistry
Keyword transition metal catalysis, C-H activation, asymmetric catalysis, cobalt catalysis
Institute The Chemical Society of Japan, The Pharmaceutical Society of Japan, The Society of Synthetic Organic Chemistry, Japan

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Abstract

Catalytic C-H activation reactions have recently attracted increasing attention in organic synthesis because they enable selective functionalization of a desired C-H bond in organic molecules. Among a variety of transition metal catalysts studied in this field, group 9 metal complexes bearing a Cp* ligand exhibit high stability and prominent catalytic efficiency. Catalytic enantioselective transformations using these types of catalysts, however, required well-designed and complex chiral Cp ligands. In this project, we try to realize catalytic stereocontrol in C-H activation reactions by developing Cp*Co(III)/chiral organocatalyst hybrid systems.

Achievement

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Original papers

  • "Cp*CoIII/Chiral Carboxylic Acid-Catalyzed Enantioselective 1,4-Addition Reactions of Indoles to Maleimides"
    Kurihara, T.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Asian Journal of Organic Chemistry,2020, 9(3), 368
  • "Catalytic Enantioselective Methylene C(sp3)-H Amidation of 8‐Alkylquinolines Using a Cp*RhIII/Chiral Carboxylic Acid System"
    Fukagawa, S.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Angewandte Chemie International Edition,2019, 58(50), 18154
  • "Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp3)-H Activation of Thioamides"
    Sekine, D.; Ikeda, K.; Fukagawa, S.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Organometallics,2019, 38(20), 3921
  • "Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System"
    Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Angewandte Chemie International Edition, 1/21/2019, 58(4), 1153
  • "One-Step Synthesis of 4H-3,1-Benzoxazin-4-ones from Weinreb Amides and 1,4,2-Dioxazol-5-ones via Cobalt-Catalyzed C-H Bond Activation"
    Tanimoto, I.; Kawai, K.; Sato, A.; *Yoshino, T.; *Matsunaga, S.
    HeteroCycles, 11/14/2018
  • "Chiral Carboxylic Acid-Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C-H Functionalization"
    *Lin, L.; Fukagawa, S.; Sekine, D.; Tomita, E.; *Yoshino, T.; *Matsunaga, S.
    Angewandte Chemie International Edition, 9/10/2018, 57(37), 12048
  • "Pentamethylcyclopentadienyl rhodium(III)-chiral disulfonate hybrid catalysis for enantioselective C-H bond functionalization"
    Satake, S.; Kurihara, T.; Nishikawa, K.; Mochizuki, T.; Hatano, M.; Ishihara, K.; *Yoshino, T.; *Matsunaga, S.
    Nature Catalysis, 7/23/2018, 1, 585
  • "Weinreb Amide Directed Versatile C−H Bond Functionalization under (η5‐Pentamethylcyclopentadienyl)cobalt(III) Catalysis"
    Kawai, K.; Bunno, Y.; *Yoshino, T.; *Matsunaga, S.
    Chemistry A European Journal, 7/17/2018, 24(40), 10231

Review

  • 「Diverse Approaches for Enantioselective C-H Functionalization Reactions Using Group 9 CpxMIII Catalysts」 *Yoshino, T.; Satake, S.; *Matsunaga, S., Chemistry A European Journal,2020
  • 「Cp*CoIII-Catalyzed C-H Functionalization and Asymmetric Reactions Using External Chiral Sources」 *Yoshino, T.; *Matsunaga, S., Synlett, 30, 1384, 12,2019

Conference

  • ICCEOCA-14
    "Chiral Carboxylic Acid-Enabled Enantioselective C–H Activation Using Rhodium(III) and Cobalt(III) Catalysts", ポスター発表
    Yoshino, T.; Fukagawa, S.; Lin, L.; Kato, Y.; Tanaka, R.; Sekine, D.; Tomita, E.; Kojima, M.; Matsunaga, S.
    9/26/2019-9/29/2019, Niseko, Japan
  • 20th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 20)
    "High-valent Rhodium- and Cobalt-catalyzed Enantioselective C-H Functionalization Reactions Using External Chiral Sources", ポスター発表
    Yoshino, T.; Fukagawa, S.; Lin, L.; Kato, Y.; Tanaka, R.; Sekine, D.; Tomita, E.; Kojima, M.; Matsunaga, S.
    7/21/2019-7/25/2019, Heidelberg, Germany
  • The 47th Naito Conference C–H Bond Activation and Transformation
    "Enantioselective Formal 1,4-Addition Reactions Through C-H Activation Using Cp*Rh(III)/Chiral Disulfonate Catalysts", ポスター発表
    Yoshino, T.; Kurihara, T,; Satake, S.; Hatano, M.; Ishihara, K.; Matsunaga, S.
    7/2/2019-7/5/2019, Sapporo, Japan
  • The 1st International Symposium on Hybrid Catalysis for Enabling Molecular Synthesis on Demand
    "Enantioselective C–H Functionalization Reactions Using High-valent Group 9 Metal Catalysts", 招待講演
    Yoshino, T.
    5/30/2019-5/31/2019, Tokyo, Japan
  • 257th ACS National Meeting & Exposition
    "Metal/organo hybrid catalysis for group 9 metal-catalyzed enantioselective C-H functionalization", 招待講演
    Yoshino, T.
    3/31/2019-4/4/2019, Orland, United States
  • The 4th Japan-Taiwan Joint Symposium for Pharmaceutical Sciences
    "New strategy for asymmetric C-H bond functionalization using Cp*Rh(III) catalyst", 招待講演
    Yoshino, T.
    8/31/2018-8/31/2018, 札幌, 日本
  • Second Japanese-Spanish Symposium in Organic Synthesis
    "New Strategy for Asymmetric C-H Bond Functionalization Using Cp*M(III) Catalysts", 招待講演
    T. Yoshino
    5/28/2018-5/29/2018, Kyoto, Japan

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