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Development of Oxidative Cyclization Reactions via C-H CleavageBased on First Row Transition Metal Catalysts

Research Project

Project/Area Number 22655027
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

MIURA Masahiro  大阪大学, 大学院・工学研究科, 教授 (20183626)

Co-Investigator(Renkei-kenkyūsha) SATOH Tetsuya  大阪大学, 大学院・工学研究科, 准教授 (40273586)
HIRANO Koji  大阪大学, 大学院・工学研究科, 助教 (70532696)
Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2010: ¥2,100,000 (Direct Cost: ¥2,100,000)
Keywords有機合成化学 / 有機金属化学 / 銅 / 分子状酸素 / 酸化カップリング・アミノ化 / アリール化 / 炭素-水素結合直接変換 / 合成化学 / 第一遷移元素 / 炭素水素結合切断 / 複素環化合物
Research Abstract

We have focused on the potential of first row transition metals, in particular, copper salts, and succeeded in the development of unique catalytic activity of copper/O2systems. Namely, the copper-catalyzed oxidative direct cyclization between N-methylanilines and electron-deficient olefins proceeded through C-H cleavage even under ambient conditions. In addition, when a similar copper/oxygen catalyst was applied to the reaction of heteroarenes with sulfoximines, the direct C-N bond formation occurred via both C-H and C-N cleavages.

Report

(3 results)
  • 2012 Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (23 results)

All 2013 2012 2011 2010 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (12 results) (of which Invited: 1 results) Remarks (1 results)

  • [Journal Article] Copper-mediated oxidative direct C-C (hetero)aromatic cross-coupling2012

    • Author(s)
      平野康次、三浦雅博
    • Journal Title

      Chem Commun

      Volume: 48巻 Pages: 10704-10714

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated and Copper-Catalyzed Cross-Coupling of Indoles and 1,3-Azoles: Double C-H Activation2012

    • Author(s)
      西野真佑子、平野康次、佐藤哲也、三浦雅博
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 51巻 Pages: 6993-6997

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated Oxidative Direct C-C (Hetero)Aromatic Cross-Coupling2012

    • Author(s)
      Hirano, Koji
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 87 Pages: 10704-10714

    • DOI

      10.1039/c2cc34659a

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated and Copper-Catalyzed Cross-Coupling of Indoles and 1,3-Azoles: Double C-H Activation2012

    • Author(s)
      Nishino, Mayuko
    • Journal Title

      Anhewandte Chemie International Edition

      Volume: 51 Pages: 6993-6997

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Oxidative Direct Cyclization of N-Methylanilines with Electron-Deficient Alkenes Using Molecular Oxygen2011

    • Author(s)
      西野真佑子、平野康次、佐藤哲也、三浦雅博
    • Journal Title

      J. Org. Chem

      Volume: 76巻 Pages: 6447-6451

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated Intermolecular Direct Biaryl Coupling2011

    • Author(s)
      北原雅典、梅田伸好、平野康次、佐藤哲也、三浦雅博
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133巻 Pages: 2160-2162

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions2011

    • Author(s)
      宮坂充、梅田伸好、平野康次、佐藤哲也、Kowalczyk Rafal、Bolm Carsten、三浦雅博
    • Journal Title

      Org. Lett

      Volume: 13巻 Pages: 359-361

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Oxidative Direct Cyclization of N-Methylanilines with Electron-Deficient Alkenes Using Molecular Oxygen2011

    • Author(s)
      Nishino, Mayuko
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 76 Issue: 15 Pages: 6447-6451

    • DOI

      10.1021/jo2011329

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated Intermolecular Direct Biaryl Coupling2011

    • Author(s)
      Miura, Masahiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Pages: 2160-2162

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions2011

    • Author(s)
      Miura, Masahiro
    • Journal Title

      Organic letters

      Volume: 13 Pages: 359-361

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 遷移金属触媒を用いる直接的芳香族カップリングの新展開2013

    • Author(s)
      三浦雅博
    • Organizer
      日本化学会第93 春季年会(2013)日本化学会学術賞受賞講演
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-24
    • Related Report
      2012 Final Research Report
  • [Presentation] Transition Metal Catalyzed Aromatic Couplings for Construction pi-Conjugated Systems2012

    • Author(s)
      三浦雅博
    • Organizer
      The 7thInternational Forum on Chemistry of Functional Organic Chemicals
    • Place of Presentation
      東京大学
    • Year and Date
      2012-11-18
    • Related Report
      2012 Final Research Report
  • [Presentation] Copper-Mediated C-H/C-H Coupling of Indoles and Azoles2012

    • Author(s)
      西野真佑子、平野康次、佐藤哲也、三浦雅博
    • Organizer
      The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都リーガロイヤルホテル
    • Year and Date
      2012-11-13
    • Related Report
      2012 Final Research Report
  • [Presentation] Copper-Mediated Intermolecular Direct Biaryl Coupling2012

    • Author(s)
      西野真佑子、平野康次、佐藤哲也、三浦雅博
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学
    • Year and Date
      2012-09-14
    • Related Report
      2012 Final Research Report
  • [Presentation] 銅塩を用いたアゾール類とインドールの直接ビアリールカップリング2012

    • Author(s)
      西野真佑子、平野康次、佐藤哲也、三浦雅博
    • Organizer
      日本化学会第92 春季年会(2012)
    • Place of Presentation
      慶応大学
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] Copper-Mediated Dehydrogenative Direct Biaryl Couplings2011

    • Author(s)
      北原雅典、梅田伸好、蜂谷斉士、平野康次、佐藤哲也、三浦雅博
    • Organizer
      The Seventh International Symposium on Integrated Synthesis (ISIS-7)
    • Place of Presentation
      シーサイドホテル舞子ビラ神戸
    • Year and Date
      2011-10-10
    • Related Report
      2012 Final Research Report
  • [Presentation] 炭素-水素結合切断を経る触媒的芳香族カップリング2010

    • Author(s)
      三浦雅博
    • Organizer
      平成22年度後期有機合成化学講習会(有機合成化学協会)
    • Place of Presentation
      東京
    • Year and Date
      2010-11-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] Copper- or Nickel-Catalyzed Direct Coupling of Heteroarenes2010

    • Author(s)
      Miura, Masahiro
    • Organizer
      3^<rd> Aachen-Osaka Joint Symposium : Biological and Chemical Approaches to Selective Processes
    • Place of Presentation
      RWTH Aachen University, Germany
    • Related Report
      2010 Annual Research Report
  • [Presentation] Copper- or Nickel-Catalyzed Direct Functionalization of Azole Compounda2010

    • Author(s)
      Miura, Masahiro
    • Organizer
      China-Japan Symposium on Catalytic Organic Synthesis
    • Place of Presentation
      Nankai University, Tianjin, China
    • Related Report
      2010 Annual Research Report
  • [Presentation] Transition Metal Catalyzed Aromatic Couplings for Construction of pi-Conjugated Systems

    • Author(s)
      Miura, Masahiro
    • Organizer
      The 7th International Forum on Chemistry of Functional Organic Chemicals
    • Place of Presentation
      東京大学
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Copper-Mediated C-H/C-H Coupling of Indoles and Azoles

    • Author(s)
      Nishino, Mayuko
    • Organizer
      The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都リーガロイヤルホテル
    • Related Report
      2011 Annual Research Report
  • [Presentation] 銅塩によるインドールとアゾールのC-H/C-Hカップリング

    • Author(s)
      西野真佑子
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学
    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~miura-lab/

    • Related Report
      2012 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2016-04-21  

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