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1991 Fiscal Year Final Research Report Summary

Tandem Carbon Carbon Bond Forming Reaction via Zincate Carbenid

Research Project

Project/Area Number 02650626
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto Institute of Technology

Principal Investigator

HARADA Toshiro  Kyoto Institute of Technology, Faculty of Engineering and Design, Associate Professor, 工芸学部, 助教授 (30135628)

Project Period (FY) 1990 – 1991
KeywordsCarbenoid / Zincate / Halogen / metal / exchange / Coupling Reaction / Palladium Catalyst
Research Abstract

The electrophilic character of carbenoids as a-metallated carbocation equivalents has not been fully demonstrated in contrast to their widely studied nucleophilic nature. In the present study, we disclosed that lithium(1bromoalkenyl)(dialkyl)zincate and lithium(1-bromocyclopropyl)(dialkyl)-zincate which can be generated by a Br/Zn exchange reaction of the corresponding gem-dibromo compounds undergo a facile intramolecular alkylation reaction to give alkenyl- and cyclopropylzinc species. Since the resulting organozinc intermediates have potential of undergoing further C-C bond formation, the reaction was extended to the tandem substitution reaction of gem-dibromo compounds via Pd(O)catalyzed arylation, acylation and alkenylation reaction.

  • Research Products

    (2 results)

All Other

All Publications (2 results)

  • [Publications] Toshiro Harada: "Novel Method for Generation of Secondary Oranozinc Reagent: Application to Tandem Carbon-Carbon Bond Formation Reaction of 1,1-Dibromoalkane" Tetrahedron Letters. 32. 1573-1576 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Novel Method for Generation of Secondary Organozinc Reagent :"Application to Tandem Carbon-Carbon Bond Formation Reaction of 1, 1-Dibromoalkane" Tetrahedron Lett. 32. 1573-1576 (1991)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-03-16  

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