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Development of Catalytic Behavior of Borderline Metal complexes and Its Applications for Organic Synthesis

Research Project

Project/Area Number 21750104
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

KOMEYAMA Kimihiro  Hiroshima University, 大学院・工学研究院, 助教 (80432681)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywords鉄触媒 / ビスマス触媒 / ヒドロアミノ化反応 / ヒドロアリール化反 / タンデム反応 / 複素環状化合物 / 芳香族縮環化合物 / ボーダーライン金属 / ヒドロアリール化反応 / 鉄 / ビスマス
Research Abstract

Borderline metal-catalyzed cycloisomerization of amino-allenes were investigated. In the reaction, we found that bismuth(III) triflate were more effective catalyst to proceed the reaction than other transition metal catalysts. The bismuth-catalyzed hydroamination can be applied to tandem ene-hydroamination of amino-allenes and amino-olefins with activated olefins and benzyl alcohols to provide multi-substituted N-heterocycles in good yields. In addition, we developed a cationic iron-catalyzed intramolecular hydroarylation of alkynes. In this reaction, the cationic iron catalyst promoted the addition of electron deficient arenes possessing strong electron-withdrawing group to alkynes, efficiently. This reactivity was very unique in comparison with other traditional catalysts for the similar hydroamination.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (19 results)

All 2011 2010 2009 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (8 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Tandem ene-reaction/hydroamination of amino-olefin and -allcnc compounds catalyzed by Bi(OTf)_32011

    • Author(s)
      Kimihiro Komeyama, Yusuke Kouya, Yuki Ohama, Ken Takaki
    • Journal Title

      Chem.Commun. 47

      Pages: 5031-5033

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Tandem ene-reaction/hydroamination of amino-olefin and-allene compounds catalyzed by Bi(OTf)_32011

    • Author(s)
      Kimihiro Komeyama, Yuusuke Kouya, Yuuki Ohama, Ken Takaki
    • Journal Title

      Chemical Communications

      Volume: (掲載決定)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes2010

    • Author(s)
      Kimihiro Komeyama, Ryoishi Igawa, Ken Takaki
    • Journal Title

      Chem.Commun. 46

      Pages: 1748-1750

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes2010

    • Author(s)
      Kimihiro Komeyama, Ryoichi Igawa, Ken Takaki
    • Journal Title

      Chemical Communications

      Volume: 39 Pages: 276-277

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes2010

    • Author(s)
      Kimihiro Komeyama
    • Journal Title

      Chemical Communications 46

      Pages: 1748-1750

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrophosphination of propargylic ether with diphenylphosphine in the presence of LiHMDS, N-heterocyclic carbene, and Ti(NMe_2)_42010

    • Author(s)
      Kimihiro Komeyama
    • Journal Title

      Chemistry Letters 39

      Pages: 276-277

    • NAID

      10027178542

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular alkynylcyclopropanation of olefins catalyzed by Bi(OTf)_3 : Stereoselective synthesis of 1-alkynyl-3-azabicyclo[3.1.0]hexanes2009

    • Author(s)
      Kimihiro Komeyama
    • Journal Title

      Angewabdte Chemie International Edition 48

      Pages: 9875-9878

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic cyclization of alkenyl N,O-acetals by Fe(OTf)_32009

    • Author(s)
      Kimihiro Komeyama
    • Journal Title

      Chemsitry Letters 38

      Pages: 724-725

    • NAID

      10025124371

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct approach to multi-substituted pyrroles from propargyl amine and 1,3-diketone or B-keto ester using Bi(OTf)_32009

    • Author(s)
      Kimihiro Komeyama
    • Journal Title

      Chemsitry Letters 38

      Pages: 224-225

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 安全・安価な金属触媒を用いた有機合成反応2010

    • Author(s)
      米山公啓
    • Organizer
      第53回産学連携フォーラム&グリーンサステイナブルケミストリーシンポジウム
    • Place of Presentation
      鳥取大学(招待講演)
    • Year and Date
      2010-09-21
    • Related Report
      2010 Annual Research Report
  • [Presentation] カチオン性鉄触媒による分子内ヒドロアリール化反応(講演番号:2F1-05)2010

    • Author(s)
      米山公啓・若宮与二・高木謙
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      近畿大学・東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] ボーダーライン金属触媒による炭素一炭素多重結合の官能基化(講演番号:2F1-35)2010

    • Author(s)
      米山公啓
    • Organizer
      日本化学会第90回春季年会第24回若い世代の特別講演会
    • Place of Presentation
      近畿大学・東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] ビスマス触媒を用いたタンデム型エン/ヒドロアミノ化反応(講演番号:1F3-37)2010

    • Author(s)
      米山公啓・神谷祐介・高木謙
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      近畿大学・東大阪
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] Intramolecular Hydroarylation of Alkynes with Electron- deficient Arenes by Iron Catalyst2009

    • Author(s)
      Kimihiro Komeyama
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry (IKOC-11)
    • Place of Presentation
      Rihga Royal Hotel Kyoto
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] Intramolecular Hydroarylation of Alkynes with Electron-deficient Arenes by Iron Catalyst2009

    • Author(s)
      Kimihiro Komeyama・Ryoichi Igawa・Tomoji Wakamiya・Ken Takaki
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都:Rihga Royal Hotel Kyoto
    • Year and Date
      2009-11-10
    • Related Report
      2010 Final Research Report
  • [Presentation] Cationic Iron-catalyzed Intramolecular Hydroarylation of Alkynes with Electron-deficient Aromatics(講演番号:P2B-04)2009

    • Author(s)
      米山公啓・井川亮一・高木謙
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学
    • Year and Date
      2009-09-10
    • Related Report
      2010 Final Research Report
  • [Presentation] Cationic Iron-catalyzed Intramolecular Hydroarylation of Alkynes with Electron-deficient Aromatics2009

    • Author(s)
      Ryoichi Igawa
    • Organizer
      有機金属化学討論会
    • Place of Presentation
      Rihga Royal Hotel Kyoto
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://home.hiroshima-u.ac.jp/kkome

    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] 多環式縮合芳香化合物の製造方法及び多環式縮合芳香族化合物2009

    • Inventor(s)
      高木謙、米山公啓
    • Industrial Property Rights Holder
      広島大学
    • Filing Date
      2009-05-05
    • Related Report
      2009 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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