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Development of New Cross-Couplings Catalyzed by Group IX Metals.

Research Project

Project/Area Number 20550043
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOkayama University

Principal Investigator

NISHIHARA Yasushi (2010)  岡山大学, 大学院・自然科学研究科, 教授 (20282858)

高木 謙太郎 (2008-2009)  Okayama University, 大学院・自然科学研究科, 教授 (80033405)

Co-Investigator(Kenkyū-buntansha) HANAYA Tadashi  岡山大学, 大学院・自然科学研究科, 准教授 (70189588)
SUEISHI Yoshimi  岡山大学, 大学院・自然科学研究科, 准教授 (50135935)
西原 康師  岡山大学, 大学院・自然科学研究科, 准教授 (20282858)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsロジウム / クロスカップリング / アリール亜鉛化合物 / アルキル求電子剤 / カルボニル化 / 酸化的Mizoroki-Heck反応 / 三成分連結反応 / ロジウム触媒 / 挿入 / 一酸化炭素 / アルケン / アルキル-アリールクロスカップリング / 三脚型配位子 / アルキルーアリールクロスカップリング / ホスホリル基
Research Abstract

Catalytic cross-coupling between carbon electrophiles andorganometallic nucleophiles is one of the most useful method to construct carbon-carbonbonds in organic synthesis. In this research, group 9 metals were used as the catalyst in place of conventional group 10 metals like nickel and palladium, intending to open new areas of cross-coupling.
As the results, two methods were developed, where, by the catalysis with rhodium, otherwise difficult cross-couplings between alkyl electrophiles and arylzinc nucleophiles successfully take place. The Rh catalysts also achieved unprecedented cross-couplingreactions between arylzinc compounds and unsaturated molecules like carbon monoxideand alkenes by the assistance of oxidants.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (11 results)

All 2011 2010 2009 2008

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (4 results)

  • [Journal Article] Rh-Catalyzed Carbonylation of Arylzinc Compounds Yielding Symmetrical Diaryl Ketones by the Assistance of Oxidizing Agents2011

    • Author(s)
      小林可奈, 西村悠吾, 高復興, 後藤和馬, 西原康師, 高木謙太郎
    • Journal Title

      Journal of Organic Chemistry

      Volume: 76巻No.6 Pages: 1949-1952

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rh-Catalyzed Carbonylation of Arylzinc Compounds Yielding Symmetrical Diaryl Ketones by the Assistance of Oxidizing Agents2011

    • Author(s)
      K.Kobayashi, Y.Nishimura, F.Gao, K.Gotoh, Y.Nishihara, K.Takagi
    • Journal Title

      Journal of Organic Chemistry

      Volume: 76 Pages: 1949-1952

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Negishi Alkyl-Aryl Cross-Coupling Catalyzed by Rh : Efficiency of Novel Tripodal 3-Diphenylphosphino-2-(diphenylphosphin o) methyl-2-methylpropyl Acetate Ligand2010

    • Author(s)
      江尻章伍, 尾藤俊介, 高橋英希, 西村悠吾, 後藤和馬, 西原康師, 高木謙太郎
    • Journal Title

      Organic Letters

      Volume: 12巻, No.8 Pages: 1692-1695

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Negishi Alkyl-Aryl Cross-Coupling Catalyzed by Rh : Efficiency of Novel Tripodal 3-Dihenylphoshino-2-(diphenylphosphino)metyl-2-methylpropyl Acetate Ligand2010

    • Author(s)
      Syogo Ejiri
    • Journal Title

      Organic Letters 12

      Pages: 1692-1695

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading toα-orβ-Phosphoryl-Substituted Alkylarenes2009

    • Author(s)
      高橋英希, 稲垣真也, 吉井奈緒子, 高復興, 西原康師, 高木謙太郎
    • Journal Title

      Journal of Organic Chemistry

      Volume: 74巻, No.7 Pages: 2794-2797

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted Alkylarenes.2009

    • Author(s)
      Hideki Takahashi
    • Journal Title

      Journal of Organic Chemistry 74

      Pages: 2794-2797

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-P(t-Bu)3-Catalyzed Consecutive Cross-Coupling of p-Phenylenedizinc Compound with Two Different Electrophiles Leading to Unsymmetrically1, 4-Disubstituted Benzenes.2008

    • Author(s)
      Takanori Kawamoto
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 1601-1604

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] アルキルヨウ化物を用いるアリール亜鉛化合物とスチレン類とのニッケル触媒三成分カップリング2011

    • Author(s)
      西村悠吾, 吉井奈緒子, 西原康師, 高木謙太郎
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Year and Date
      2011-09-09
    • Related Report
      2010 Final Research Report
  • [Presentation] Pd-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Using (o-Methoxyphenyl) diphenylphosphine as a Ligand2010

    • Author(s)
      Y.Nishimura, S.Odo, Y.Nishihara, K.Takagi
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] パラジウム触媒根岸型アルキルアリールクロスカップリング : アリールホスフィン配位子の有効性2009

    • Author(s)
      西村悠吾
    • Organizer
      日本化学会西日本大会2009
    • Place of Presentation
      愛媛大学城北キャンパス
    • Year and Date
      2009-11-08
    • Related Report
      2009 Annual Research Report
  • [Presentation] 根岸型アルキルーアyールクロスカツプリング : 配位性官能基を有するホスフィン配位子によるβ一水素脱離の抑制2008

    • Author(s)
      尾藤俊介
    • Organizer
      第55回有機金夙化学討論会
    • Place of Presentation
      大阪府立大学中百舌鳥キャンパス
    • Year and Date
      2008-09-29
    • Related Report
      2008 Annual Research Report

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

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