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Development of redox neutral bond formation with transition metal catalyst

Research Project

Project/Area Number 15H03809
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

Kurahashi Takuya  京都大学, 工学研究科, 准教授 (50432365)

Project Period (FY) 2015-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2018: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2017: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2016: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2015: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Keywords遷移金属 / 酸化還元調和型 / XAFS / EXAFS / XANES / EPR / DFT / ニッケル / 酸化還元調和型反応 / カルボハロゲン化反応 / 遷移金属触媒 / 理論化学計算 / 溶液XAFS測定 / EPR測定 / 溶液 X 線吸収微細構造解析 / 3d遷移金属触媒 / ニッケル触媒 / 溶液XAFS / 炭素骨格構築法 / 触媒的不斉合成 / アリルアルコール / 遷移金属触媒反応 / 不斉触媒反応 / 炭素骨格構築 / 不斉合成 / 不斉配位子 / 反応機構解析 / 量子化学計算 / X線吸収分光法
Outline of Final Research Achievements

In organic synthesis, bond formation is one of the most basic and important transformation, and is essential in the construction of the molecular skeleton. However, conventional organic synthesis methods are often not efficient because they often require "pre-activation by respective oxidation and reduction of substrates" to achieve bond formation. In this research project, we developed a highly efficient carbon framework construction method by redox neutral reaction, in which activation by oxidation / reduction of substrates is not required in advance.

Academic Significance and Societal Importance of the Research Achievements

化学結合の形成は有機合成における基本的な反応であるにも関わらず、未だ解決すべき課題が多い。多くの場合は結合を直接的に形成することは困難であり、基質の反応部位を予め各々酸化または還元することにより官能基を導入して活性化する必要がある。基質に含まれる他の官能基の保護および結合形成反応後の脱保護、そして酸化剤や還元剤の使用に伴う廃棄物が生じるので原子効率が悪い。さらに複数の反応による多段階工程が必要であるなど作業効率も良くない。本課題研究では、現代社会に求められている低環境負荷・高効率な炭素―炭素結合や炭素―ヘテロ原子結合の構築法の開発を実施した。

Report

(5 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (8 results)

All 2019 2018 2017

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Open Access: 1 results) Presentation (2 results)

  • [Journal Article] Diastereoselective Synthesis of 1,3-Oxazolidines via Cationic Iron Porphyrin-catalyzed Cycloaddition of Aziridines with Aldehydes2019

    • Author(s)
      Teranishi Satoru、Maeda Kazuki、Kurahashi Takuya、Matsubara Seijiro
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 8 Pages: 2593-2596

    • DOI

      10.1021/acs.orglett.9b00560

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cationic Cobalt Porphyrin-Catalyzed Allylation of Aldehydes with Allyltrimethylsilanes2019

    • Author(s)
      Rei Tomifuji, Shota Masuda, Takuya Kurahashi, and Seijiro Matsubara
    • Journal Title

      Organic Letters

      Volume: 印刷中 Issue: 10 Pages: 3834-3837

    • DOI

      10.1021/acs.orglett.9b01303

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Aza-Diels Alder Reaction with Ion-Paired ; Iron Lewis Acid ; Brønsted Acid Catalyst2019

    • Author(s)
      Rei Tomifuji, Takuya Kurahashi, and Seijiro Matsubara
    • Journal Title

      Chem. Eur. J

      Volume: 印刷中 Issue: 38 Pages: 8987-8991

    • DOI

      10.1002/chem.201901563

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed Intermolecular Carboiodination of Alkynes with Aryl Iodides2018

    • Author(s)
      Takahashi, T.; Kuroda, D.; Kuwano, T.; Yoshida, Y.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 90 Pages: 12750-12753

    • DOI

      10.1039/c8cc07560c

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] FeCl3 as an Ion-Pairing Lewis Acid Catalyst. Formation of Highly Lewis Acidic FeCl2+ and Thermodynamically Stable FeCl4 To Catalyze the Aza-Diels-Alder Reaction with High Turnover Frequency2018

    • Author(s)
      Tomifuji, R.; Maeda, K.; Takahashi, T.; Kurahashi, T.; Matsubara, S.
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 23 Pages: 7474-7477

    • DOI

      10.1021/acs.orglett.8b03249

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ligand-controlled Behavior of Ag(I) π Complex as σ-Lewis Acid,2018

    • Author(s)
      K. Maeda, T. Takahashi, R. Tomifuji, N. Hirao, T. Kurahashi, S. Matsubara
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 4 Pages: 532-535

    • DOI

      10.1246/cl.180052

    • NAID

      130006638878

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] ニッケル触媒を用いるアルキンのカルボハロゲン 化2017

    • Author(s)
      高橋 俊文・倉橋 拓也・松原 誠二郎
    • Organizer
      有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 鉄カチオン種の発生を利用した強ルイス酸触媒に よるアルデヒドと非活性型ジエンの不斉ヘテロディー ルスアルダー反応2017

    • Author(s)
      冨藤 玲・倉橋 拓也 ・松原 誠二郎
    • Organizer
      有機金属化学討論会
    • Related Report
      2017 Annual Research Report

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Published: 2015-04-16   Modified: 2021-01-27  

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