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2012 Fiscal Year Final Research Report

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

Research Project

  • PDF
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
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
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.

  • Research Products

    (12 results)

All 2013 2012 2011 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (6 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

    • 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

    • 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

    • 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

    • 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

    • 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [Remarks]

    • URL

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

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Published: 2014-08-29   Modified: 2015-10-15  

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