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Development of clean and efficient method for the preparation of organophosphorus compounds

Research Project

Project/Area Number 16350027
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionNational Institute of Advanced Industrial Science and Technology

Principal Investigator

HAN Li-Biao  National Institute of Advanced Industrial Science and Technolog, search Institute for Innovation in Sustainable Chemistry, Senior Research Scientist, 環境化学技術研究部門, 主任研究員 (30356860)

Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥15,300,000 (Direct Cost: ¥15,300,000)
Fiscal Year 2006: ¥4,500,000 (Direct Cost: ¥4,500,000)
Fiscal Year 2005: ¥5,100,000 (Direct Cost: ¥5,100,000)
Fiscal Year 2004: ¥5,700,000 (Direct Cost: ¥5,700,000)
KeywordsOrganophosphorus compounds / Preparation / Catalyst / Optically active compounds / Selectivity / 立体特異的 / P-キラリティー / 不斉付加 / 不斉 / 求核置換反応 / ラジカル付加 / ニッケル触媒 / ヒドロホスホリル化 / ニッケルヒドリド錯体 / リン置換ブタジエン / プロパルギルアルコール
Research Abstract

Diphenylphosphine oxide and related P(0)-H compounds react with propargyl alcohols at room temperature in the presence of a catalytic amount of Ni(0) complex and Ph2P(0)OH to produce high yields of phosphinoyl 1,3-dienes though an efficient in situ dehydration process. On the other hand, by using Josiphos ligands, palladium-catalyzed hydrophosphorylation of norbornenes with hydrogen phosphonates proceeded efficiently to give the corresponding phosphonates in high enantioselectivities. More over, a variety of functionalized optically pure (RP)-alkylphenylphosphinates are readily prepared by stereospecific radical or base-catalyzed additions of the easily available (RP)-menthyl phenylphosphinate to alkenes.

Report

(5 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Products Report
  • Research Products

    (13 results)

All 2012 2007 2006 2005 2004

All Journal Article (5 results) Book (1 results) Patent(Industrial Property Rights) (7 results) (of which Overseas: 1 results)

  • [Journal Article] Nickel-catalyzed Addition of P(0) - H Bonds to Propargyl Alcohols : One-Pot Generation of Phosphinoyl 1,3-Butadienes2005

    • Author(s)
      韓 立彪 他
    • Journal Title

      Organic Letters 7・14

      Pages: 2909-2911

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Stereospecific Addition of H-P Bond to Alkenes : A Simple Method for the Preparation of (RP)-Phenylphosphinates2005

    • Author(s)
      韓 立彪 他
    • Journal Title

      Journal of Organic Chemistry 70・24

      Pages: 10121-10123

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Nickel-catalyzed Addition of P(O)-H Bonds to Propargyl Alcohols : One-Pot Generation of Phosphinoyl 1, 3-Butadienes2005

    • Author(s)
      Li-Biao Han
    • Journal Title

      Organic Letters 7・14

      Pages: 2909-2911

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Stereospecific Addition of H-P Bond t Alkenes : A Simple Method for the Preparation of (RP)-Phenylphosphinates2005

    • Author(s)
      Li-Biao Han
    • Journal Title

      Journal of Organic Chemistry 70.24

      Pages: 10121-10123

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Nickel-catalyzed Addition of P(O)-H Bonds to Propargyl Alcohols : One-Pot Generation of Phosphinoyl 1,3-Butadienes2005

    • Author(s)
      韓 立彪 他
    • Journal Title

      Organic Letters 7・14

      Pages: 2909-2911

    • Related Report
      2005 Annual Research Report
  • [Book] 第5版 実験化学講座 23 -無機化合物-2005

    • Author(s)
      韓 立彪など(共著)
    • Total Pages
      554
    • Publisher
      丸善株式会社
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性リン化合物の製造方法2012

    • Inventor(s)
      韓 立彪, 徐 清
    • Industrial Property Rights Holder
      独立行政法人産業技術総合研究所
    • Industrial Property Rights Type
      特許
    • Acquisition Date
      2012-04-06
    • Related Report
      Products Report
  • [Patent(Industrial Property Rights)] 光学活性リン化合物の製造方法2007

    • Inventor(s)
      韓 立彪, Xu Qing
    • Industrial Property Rights Holder
      独立行政法人産業技術総合研究所
    • Industrial Property Rights Type
      特許
    • Filing Date
      2007-08-20
    • Related Report
      Products Report
    • Overseas
  • [Patent(Industrial Property Rights)] 光学活性リン化合物の製造方法2006

    • Inventor(s)
      韓 立彪, Xu Qing
    • Industrial Property Rights Holder
      産業技術総合研究所
    • Industrial Property Number
      2006-248707
    • Filing Date
      2006-09-13
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 光学活性リン化合物及びその製造方法2005

    • Inventor(s)
      韓 立彪, Zhao Chanq-Qiu
    • Industrial Property Rights Holder
      産業技術総合研究所
    • Industrial Property Number
      2005-174194
    • Filing Date
      2005-06-14
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性ホスホン酸エステル類の製造方法2005

    • Inventor(s)
      韓 立彪, Xu Qing
    • Industrial Property Rights Holder
      産業技術総合研究所
    • Industrial Property Number
      2005-003352
    • Filing Date
      2005-11-21
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Patent(Industrial Property Rights)] フェニルホスフィン酸メンチルの製造方法2005

    • Inventor(s)
      韓 立彪
    • Industrial Property Rights Holder
      産業技術総合研究所
    • Filing Date
      2005-11-12
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] フェニルホスフィン酸メンチルの製造方法2004

    • Inventor(s)
      韓 立彪
    • Industrial Property Rights Holder
      産業技術総合研究所
    • Industrial Property Number
      2004-329205
    • Filing Date
      2004-11-12
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary

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Published: 2004-04-01   Modified: 2017-02-24  

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