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2005 Fiscal Year Final Research Report Summary

Nickel/Zinc Chloride-Promoted Domino Reaction of polyenynes

Research Project

Project/Area Number 16590010
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionNagoya City University

Principal Investigator

IKEDA Shin-ichi  Nagoya City University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究科, 助教授 (90254309)

Project Period (FY) 2004 – 2005
Keywordsnickel / zinc chloride / enone / dienyne / domino process
Research Abstract

A Ni(0)/ZnCl_2 system effectively promotes the coupling of enones and alkene-tethered alkynes. In the reaction with 1,6-enynes, the oxidative cyclization of Ni(0) species on enones across the alkyne part followed by ZnCl_2-promoted cleavage generates alkenylnickel intermediates. Subsequent migratory insertion of the tethered alkene occurs with 5-exo-cyclization. When the resulting alkylnickel intermediates have β-hydrogen atoms, the reaction terminates by β-hydrogen elimination to provide cyclopentane derivatives. On the other hand, an alkylnickel intermediate that does not have β-hydrogen atoms undergoes the insertion of a second alkene unit to cause a domino effect via a three-fold C-C bond formation process.

  • Research Products

    (3 results)

All 2005 2004

All Journal Article (2 results) Book (1 results)

  • [Journal Article] Ni-Catalyzed, ZnCl_2-Assisted Domino Coupling of Enones, Alkynes, and Alkenes2004

    • Author(s)
      S.Ikeda, R.Sanuki, et al.
    • Journal Title

      J.Am.Chem.Soc. 126・33

      Pages: 10331-10338

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Ni-Catalyzed, ZnCl_2-Assisted Domino Coupling of Enones, Alkynes, and Alkenes2004

    • Author(s)
      S.Ikeda
    • Journal Title

      J.Am.Chem.Soc. Vol.126, No.33

      Pages: 10331-10338

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Modern Organonickel Chemistry, Chapter 4.Reaction with Alkynes2005

    • Author(s)
      Shin-ichi Ikeda
    • Total Pages
      35
    • Publisher
      Wiley-VCH
    • Description
      「研究成果報告書概要(和文)」より

URL: 

Published: 2007-12-13  

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