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New Approaches for Creating New Phosphines and Their Applications

Research Project

Project/Area Number 18065014
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionKyoto University

Principal Investigator

OSHIMA Koichiro  Kyoto University, 大学院・工学研究科, 教授 (00111922)

Project Period (FY) 2006 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥33,600,000 (Direct Cost: ¥33,600,000)
Fiscal Year 2009: ¥8,400,000 (Direct Cost: ¥8,400,000)
Fiscal Year 2008: ¥8,400,000 (Direct Cost: ¥8,400,000)
Fiscal Year 2007: ¥8,400,000 (Direct Cost: ¥8,400,000)
Fiscal Year 2006: ¥8,400,000 (Direct Cost: ¥8,400,000)
Keywords選択的合成・反応 / ホスフィン配位子 / 環化付加 / インドール / 立体障害 / 鈴木カップリング / パラジウム触媒 / ホスフィン / 均一系分子触媒 / 配位子 / 協奏機能 / かさ高い配位子 / 交差カップリング反応 / 二座配位子 / ヒドロホスフィン化 / 1-アルキニルホスフィン
Research Abstract

Due to the importance of organophosphines as ligands for transition metal catalysts, development of efficient methods for the synthesis of new phosphines is very important. We recognized 1-alkynylphosphines and their derivatives as useful precursors for creation of new phosphines. Chemical modifications of the carbon-carbon triple bonds, including nucleophilic addition and cycloaddition, led to a wide range of new useful phosphines that are otherwise difficult to synthesize.

Report

(6 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report   Self-evaluation Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • Research Products

    (24 results)

All 2010 2008 2007 2006 Other

All Journal Article (23 results) (of which Peer Reviewed: 14 results) Remarks (1 results)

  • [Journal Article] Synthesis of 2-Indolylphosphines by Palladium-Catalyzed Annulation of 1-Alkynyl phosphine Sulfides with 2-Iodoanilines2010

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Organic Letters 12

      Pages: 1476-1479

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1-Alkynylphosphines and Their Derivatives as Key Starting Materials in Creating New Phosphines2010

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Chemistry-An Asian Journal 5

      Pages: 398-409

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bulky Arylphosphanes by Rhodium-Catalyzed Formal [2 + 2 + 2] Cycloaddition Reaction and Their Use as Ligands.2008

    • Author(s)
      Takayuki Kobatake, Azusa Kondoh, Suguru Yoshida, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Chem. Asian J. 3

      Pages: 1613-1619

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Aryl Sulfides and Alkenyl Alkyl Sulfides with Alkyl Grignard Reagents by Using (Z)-3, 3-Dimethyl-1, 2-bis(diphenyl- phosphino)but-1-ene as Ligand.2008

    • Author(s)
      Shigenari Kanemura, Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Synthesis

      Pages: 2659-2664

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Regio- and Stereoselective Hydroamidation of 1-Alkynylphosphine Sulfides Catalyzed by Cesium Base.2008

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Org. Lett. 10

      Pages: 3093-3095

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Regio- and Stereoselective Additions of Diphenyldithiophosphinic Acid to N-(1-Alkynyl)amides and 1-Alkynyl Sulfides.2008

    • Author(s)
      Shigenari Kanemura, Azusa Kondoh, Hiroto Yasui, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Bull. Chem. Soc. Jpn. 81

      Pages: 506-514

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Reaction of 1-Alkynylphosphines with Water Yielding (E)-1-Alkenylphosphine Oxides.2008

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Bull. Chem. Soc. Jpn. 81

      Pages: 502-505

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bulky Arylphosphanes by Rhodium-Catalyzed Formal [2 + 2 + 2] Cycloaddition Reaction and Their Use as Ligands2008

    • Author(s)
      Takayuki Kobatake, Azusa Kondoh, Suguru Yoshida, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      Chem. Asian J. 3

      Pages: 1613-1619

    • Related Report
      2008 Self-evaluation Report
  • [Journal Article] Regio- and Stereoselective Hydroamidation of 1-Alkynylphosphine Sulfides Catalyzed by Cesium Base2008

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      Org. Lett. 10

      Pages: 3093-3095

    • Related Report
      2008 Self-evaluation Report
  • [Journal Article] Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Aryl Sulfides and Alkenyl Alkyl Sulfides with Alkyl Grignard Reagents by Using (Z)-3, 3-Dimethy1-1, 2bis(diphenylphosphino)but-l-ene as Ligand2008

    • Author(s)
      Kanemura, S. ; Kondoh, A. ; Yorimitsu, H. ; Oshima , K.
    • Journal Title

      Synthesis

      Pages: 2659-2664

    • Related Report
      2008 Annual Research Report
  • [Journal Article] Synthesis of Bulky Arylphosphanes by Rhodium-Catalyzed Formal [2+2+2] Cycloaddition Reaction and Their Use as Ligands2008

    • Author(s)
      Kobatake, T. ; Kondoh, A. ; Yoshida, S. ; Yorimitsu, H. ; Oshima, K
    • Journal Title

      Chem. Asian J. 2

      Pages: 1613-1619

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bulky Phosphines by Rhodium-Catalyzed Formal [2 + 2 + 2] Cycloaddition Reactions of Tethered Diynes with 1-Alkynylphosphine Sulfides.2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 6996-6997

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-catalyzed anti-Hydrophosphination Reaction of 1-Alkynylphosphines with Diphenylphosphine Providing (Z)-1, 2-Diphosphino-1-alkenes.2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 4099-4104

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed anti-Hydrothiolation of 1-Alkynylphosphines.2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Org. Lett. 9

      Pages: 1383-1385

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bulky Phosphines by Rhodium-Catalyzed Formal [2 + 2 + 2] Cycloaddition Reactions of Tethered Diynes with 1-Alkynylphosphine Sulfides2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 6996-6997

    • Related Report
      2008 Self-evaluation Report
  • [Journal Article] Copper-catalyzed anti-Hydrophosphination Reaction of 1-Alkynylphosphines with Diphenylphosphine Providing (Z)-1,2-Diphosphino-1-alkenes2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 4099-4104

    • Related Report
      2008 Self-evaluation Report
  • [Journal Article] Palladium-Catalyzed anti-Hydrothiolation of 1-Alkynylphosphines2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      Org. Lett. 9

      Pages: 1383-1385

    • Related Report
      2008 Self-evaluation Report
  • [Journal Article] Palladium-Catalyzed anti-Hydrothiolation of 1-Alkynylphosphines2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      Organic Letters 9

      Pages: 1383-1385

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbocupration of 1-Alkynylphosphines Followed by Trapping with Electrophiles2007

    • Author(s)
      Shigenari Kanemura, Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      Organic Letters 9

      Pages: 2031-2033

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bulky Phosphines by Rhodium-Catalyzed Formal [2+2+2] Cycloaddition Reactions of Tethered Diynes with 1-Alkynylphosphine2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 6996-6997

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed anti-Hydrothiolation of 1-Alkynylphosphines2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Organic Letters 8(in press)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Copper-catalyzed anti-Hydrophosphination Reaction of 1-Alkynylphosphines with Diphenylphosphine Providing (Z)-1,2-Diphosphino-l-alkenes2007

    • Author(s)
      Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Journal of the American Chemical Society 129(in press)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Radical Phosphination of Organic Halides and Alkyl Imidazole-1-carbothioates2006

    • Author(s)
      Akinori Sato, Hideki Yorimitsu, Koichiro Oshima
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 4240-4241

    • Related Report
      2006 Annual Research Report
  • [Remarks]

    • URL

      http://concerto.cstm.kyushu-u.ac.jp/

    • Related Report
      2008 Self-evaluation Report

URL: 

Published: 2006-04-01   Modified: 2018-03-28  

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