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Implementation of a new strategy in transition metal catalyzed functionalization of the sp3 carbon-hydrogen bond of carbonyl and amine compounds

Research Project

Project/Area Number 16K05773
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionNational Institute of Advanced Industrial Science and Technology

Principal Investigator

Yada Akira  国立研究開発法人産業技術総合研究所, 材料・化学領域, 研究員 (70619965)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords炭素ー水素結合活性化 / 遷移金属触媒 / 窒素ー酸素結合切断 / 有機金属化学 / 炭素―水素結合 / 不活性結合活性化 / 官能基化
Outline of Final Research Achievements

In this research project, transition metal catalyzed sp3-carbon-hydrogen bond functionalization of carbonyl compounds and amine compounds, which are otherwise difficult to activate and functionalize previously, is studied in order to improve the practicality and efficiency of the C-H bond functionalization reaction. As the result, palladium-catalyzed carbon monoxide insertion reaction into the C-H bond at the β-position of N-carboxyl amine to furnish β-lactam is found. The reaction undergoes through the cleavages of nitrogen-oxygen and carbon-hydrogen bond in the molecule, which is scientifically interesting and mechanistically unprecedent.

Academic Significance and Societal Importance of the Research Achievements

本研究で得られた成果は、1つの分子内で窒素-酸素結合と炭素-水素結合の2種類の結合の切断を伴うというこれまでにほとんど知られていない形式で進行するものであり、学術的に極めて興味深いものである。また、標的分子の合成する工程を短縮できたり副生成物を最小限に抑えることもできるため、環境調和に優れた次世代型プロセスとして期待できる。さらに研究を進展させることによって、汎用性が高い炭素-水素結合の直接活性化・官能基化反応の開発につながることが期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (7 results)

All 2019 2018 2017

All Journal Article (3 results) (of which Peer Reviewed: 1 results) Presentation (3 results) Book (1 results)

  • [Journal Article] 人工知能による触媒反応の予測 (キャタリストインフォマティクス)2019

    • Author(s)
      矢田陽、佐藤一彦
    • Journal Title

      化学と教育

      Volume: 67 Pages: 70-73

    • NAID

      130007793414

    • Related Report
      2018 Annual Research Report
  • [Journal Article] 人工知能(AI)による触媒反応の収率予測技術2018

    • Author(s)
      矢田陽、佐藤一彦
    • Journal Title

      配管技術

      Volume: 60 Pages: 1-5

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Palladium-Catalyzed Dehydrogenative Coupling Reaction of Terminal Alkynes with Unactivated Alkenes2018

    • Author(s)
      Yada Akira、Nishi Shoki、Sato Yuta、Ichinoseki Sakina、Murakami Masahiro
    • Journal Title

      Journal of the Chinese Chemical Society

      Volume: 65 Issue: 1 Pages: 117-121

    • DOI

      10.1002/jccs.201700268

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 有機合成化学者が挑戦するAI×触媒研究2018

    • Author(s)
      矢田陽
    • Organizer
      「AIと有機合成化学」第2回勉強会
    • Related Report
      2018 Annual Research Report
  • [Presentation] キャタリストインフォマティクス ~触媒の自動発見を目指して~2018

    • Author(s)
      矢田陽
    • Organizer
      第2回 産総研化学研究シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] サリチルアルデヒドを配向基として利用した炭素-水素結合の活性化反応2017

    • Author(s)
      矢田 陽、廖文卿、石原優実、佐藤裕太、村上正浩
    • Organizer
      第6回 JACI/G SCシンポジウム
    • Related Report
      2017 Research-status Report
  • [Book] 触媒技術の動向と展望20192019

    • Author(s)
      矢田陽、佐藤一彦
    • Total Pages
      524
    • Publisher
      触媒学会
    • Related Report
      2018 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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