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Challenging C-C Bond Formation via Degassing Reactions on Acid Anhydrides

Research Project

Project/Area Number 18K14868
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionOsaka University

Principal Investigator

Yahata Kenzo  大阪大学, 大学院薬学研究科, 助教 (30808100)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords炭素ー炭素結合形成 / 4級炭素 / ビアリール / 有機合成化学 / 遷移金属化学
Outline of Final Research Achievements

We developed transition metal complex-mediated decarboxylation and decarbonylation reaction on acid anhydrides, which enables new carbon-carbon bond formation reactions to give ketones and biaryls.
Furthermore, we developed decatungstate catalyzed formal dehydrogenative coupling between non-activated hydrocarbons and aldehydes.
The molecules, i.e. ketones and biaryls, obtained by these methodologies are ones of important functional molecules in the fields of organic synthesis, metal ligand chemistry, and material sciences.

Academic Significance and Societal Importance of the Research Achievements

炭素-炭素結合は有機分子を構成する基本単位である。本研究では従来法では形成が困難な炭素-炭素結合の形成や従来法では原料として利用困難であった単純な分子、すなわち安価な分子、の有用な化合物への変換を達成できる可能性を示した。今回開発した手法で合成可能な分子は有機合成や金属配位子、有機材料など幅広い分野で重要な分子群である。
また、新たに開発した脱水素型カップリング反応は反応の進行に光と酸素というクリーンなエネルギーを利用して進行するため、持続可能な社会を実現するための足掛かりとして重要な知見を与えると考えられる。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (12 results)

All 2020 2019

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (8 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Cobalt-Catalyzed Hydroamination of Alkenes with 5-Substituted Tetrazoles: Facile Access to 2,5-Disubstituted Tetrazoles and Asymmetric Intermolecular Hydroaminations2020

    • Author(s)
      Yahata Kenzo、Kaneko Yuki、Akai Shuji
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 68 Issue: 4 Pages: 332-335

    • DOI

      10.1248/cpb.c20-00068

    • NAID

      130007824859

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2020-04-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-Pot Formal Dehydrogenative Ketone Synthesis from Aldehydes and Non-activated Hydrocarbons2020

    • Author(s)
      Yahata Kenzo、Yoshioka Shin、Hori Shuhei、Sakurai Shu、Kaneko Yuki、Hasegawa Kai、Akai Shuji
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 68 Issue: 4 Pages: 336-338

    • DOI

      10.1248/cpb.c20-00075

    • NAID

      130007824858

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2020-04-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Intermolecular Markovnikov Hydroamination of Nonactivated Olefins: N2-Selective Alkylation of Benzotriazole2020

    • Author(s)
      Yahata Kenzo、Kaneko Yuki、Akai Shuji
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 2 Pages: 598-603

    • DOI

      10.1021/acs.orglett.9b04375

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Coupling Reaction between Aldehydes and Non-Activated Hydrocarbons via the Reductive Radical-Polar Crossover Pathway2020

    • Author(s)
      Yahata Kenzo、Sakurai Shu、Hori Shuhei、Yoshioka Shin、Kaneko Yuki、Hasegawa Kai、Akai Shuji
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 3 Pages: 1199-1203

    • DOI

      10.1021/acs.orglett.0c00096

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] 硫酸オキソバナジウムを用いたアリルアルコール、ベンジルアルコール類の直接的求核置換反応2020

    • Author(s)
      長谷川魁、吉岡晋、八幡健三、赤井周司
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] コバルト触媒を用いたベンゾトリアゾールのN2 選択的アルキル化反応の開発2019

    • Author(s)
      金子祐樹, 八幡健三, 赤井周司
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Bryostatin類の合成研究―高活性化合物類縁体の包括的合成研究―2019

    • Author(s)
      桜井秋、八幡健三、赤井周司
    • Organizer
      第69回日本薬学会関西支部総会・大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ビリジンの合成研究―集積した官能基の位置及び立体選択的構築―2019

    • Author(s)
      堀修平、杉山公二、八幡健三、赤井周司
    • Organizer
      第69回日本薬学会関西支部総会・大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthetic Study of Bryostatins2019

    • Author(s)
      Shu Sakurai, Kenzo Yahata, Shuji Akai
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic study of the furanosteroid, viridin2019

    • Author(s)
      Shuhei Hori, Koji Sugiyama, Kenzo Yahata, Shuji Akai
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] N2-Selective Alkylation of Benzotriazoles via Cobalt Catalyzed Hydroamination Reaction of Non-Activated Olefins2019

    • Author(s)
      Yuki Kaneko, Kenzo Yahata, Shuji Akai
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Bryostatin類の合成研究2019

    • Author(s)
      桜井秋、八幡健三、赤井周司
    • Organizer
      第39回有機合成若手セミナー
    • Related Report
      2019 Annual Research Report

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Published: 2018-04-23   Modified: 2021-02-19  

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