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New synthetic methodology of heterocycles based on ubiquitous metal catalysts

Research Project

Project/Area Number 20613010
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Element strategy
Research InstitutionHiroshima University

Principal Investigator

TAKAKI Ken  Hiroshima University, 大学院・工学研究科, 教授 (80116615)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2008: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsユビキタス金属 / 触媒 / 複素環 / ボーダーライン触媒 / 鉄触媒 / ビスマス触媒 / 環化反応 / ピロール / N,O-アセタール / ヒドロアリール化反応 / ボーダーライン金属触媒 / ビスマス / 鉄
Research Abstract

Ubiquitous metals like iron and bismuth have been found to act as very reactive borderline catalysts due to their π- and σ-acidities. Based on these characteristics, intramolecular carbo-oxycarbonylation of 3-alkynyl esters, pyrrole synthesis from 2-propynylamines and 1,3-diketones, cyclization of alkenyl N,O-acetals, alkynylcyclopropanation of 1,6-enynes, and intramolecular hydroarylation of alkynes have been succeeded very effectively under mild conditions, which provide new synthetic methods for many useful heterocycles.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (21 results)

All 2010 2009 2008

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (7 results)

  • [Journal Article] Cationic Iron-Catalyzed Intramolecular Alkyne-hydroarylation with Electron-deficient Arenes.2010

    • Author(s)
      K. Komeyama, R. Igawa, K. Takaki
    • Journal Title

      Chem. Commun 46

      Pages: 1748-1750

    • Related Report
      2009 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 46

      Pages: 1748-1750

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Alkynylcyclopropanation of Olefins Catalyzed by Bi(OTf)3: Stereoselective Synthesis of 1-Alkyny1-3-azabicyclo[3, 1, 0]hexanes.2009

    • Author(s)
      K. Komeyama, N. Saigo, M. Miyagi K. Takaki
    • Journal Title

      Angew. Chem Int. Ed. 48

      Pages: 9875-9878

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Cyclization of Alkenyl N, O-Acetals by Fe(OAc)3.2009

    • Author(s)
      K. Komeyama, R. Igawa, T. Morimoto, K. Takaki
    • Journal Title

      Chemistry Letters 38(7)

      Pages: 724-725

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct Approach to Multi-substituted Pyrroles from 2-Propynylamine and 1, 3-Diketones or β-Keto Esters Using Bi(OTf)3 Catalyst.2009

    • Author(s)
      K. Komeyama, M. Miyagi, K. Takaki
    • Journal Title

      Chemistry Letters 38(3)

      Pages: 224-225

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic cyclization of alkenyl N, O-acetals by Fe(OTf)32009

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

      Chemistry Letters 38

      Pages: 724-725

    • 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, Natsuko Saigo, Motoyoshi Miyagi, Ken Takaki
    • Journal Title

      Angewandte Chemie International Edition 48

      Pages: 9875-9878

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct approach to multi-substituted pyrroles from propargyl amine and 1, 3-diketone or β-keto ester using Bi(0Tf)3.2009

    • Author(s)
      Kimihiro. Komevama. Motovoshi Miyagi. Ken Takaki
    • Journal Title

      Chemistry Letters 38

      Pages: 224-225

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth-catalyzed Intramolecular Carbo-oxycarbonylaton of 3-Alkynyl Esters.2008

    • Author(s)
      K. Komeyama, K. Takahashi, K. Takaki
    • Journal Title

      Organic Letters 10(22)

      Pages: 5119-5122

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth-catalyzed Intramolecular Hydro-oxycarbonylation of Alkynes.2008

    • Author(s)
      K. Komeya-ma, K. Takahashi, K. Takaki
    • Journal Title

      Chemistry Letters 37(6)

      Pages: 602-603

    • NAID

      10021081087

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth-catalyzed Cyclization of Amino-1, 6-enynes.2008

    • Author(s)
      K. Komeyama, M. Miyagi, K. Takaki
    • Journal Title

      Hetaroatom Chemistry 19(6)

      Pages: 644-648

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth-catalyzed intramolecular carbo-oxycarbonylation of 3-alkynyl esters.2008

    • Author(s)
      Kimihiro Komeyama, Keita Takahashi, Ken Takaki
    • Journal Title

      Organic Letters 10

      Pages: 5119-5122

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth-catalyzed cyclization of amino-1.6-enynes.2008

    • Author(s)
      Kimihiro Komeyama, Motoyoshi Miyagi, Ken Takaki
    • Journal Title

      Heteroatom Chemistry 19

      Pages: 644-648

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bismuth-catalyzed intramolecuar hydro-oxycarbonylation of alkynes2008

    • Author(s)
      Kimihiro Komeyama, Keita Takahashi., Ken Takaki
    • Journal Title

      Chemistry Letters 37

      Pages: 602-603

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [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2010

    • Author(s)
      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
      2009 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2010

    • Author(s)
      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
      2009 Final Research Report
  • [Presentation] Intramolecular Hydroarylation of Alkynes with Electron-deficient Arenes by Iron Catalyst2009

    • Author(s)
      高木謙
    • Organizer
      IKOCK-11
    • Place of Presentation
      京都
    • Year and Date
      2009-09-11
    • Related Report
      2009 Final Research Report
  • [Presentation] カチオン性鉄触媒を用いた電子不足芳香環のアルキンへの分子内ヒドロアリール化反応2009

    • Author(s)
      井川亮一, 米山公啓, 高木謙
    • Organizer
      第56回有機金属討論会
    • Place of Presentation
      同志社大学
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] カチオン性鉄錯体を触媒とする芳香族置換アルキンの分子内ヒドロアリール化反応2009

    • Author(s)
      井川亮一, 米山公啓, 高木謙
    • Organizer
      日本化学会第89回春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] ビスマス触媒を用いたエンイノール類のアルキニルシクロプロパン化反応2009

    • Author(s)
      米山公啓, 宮城元嘉, 高木謙
    • Organizer
      日本化学会第89回春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] Borderline Metal-Catalyzed Heterofunctionalization of Alkyne2008

    • Author(s)
      米山公啓, 高橋慶多, 高木謙
    • Organizer
      第55回有機金属化学討論会
    • Place of Presentation
      大阪府立大学
    • Year and Date
      2008-10-28
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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