Nickel-Catalyzed Allylic Substitution of Simple Alkenes

Authors

  • Dr. Ryosuke Matsubara,

    1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-492, Cambridge, MA 02139 (USA), Fax: (+1) 617-324-0253
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  • Prof. Dr. Timothy F. Jamison

    Corresponding author
    1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-492, Cambridge, MA 02139 (USA), Fax: (+1) 617-324-0253
    • Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-492, Cambridge, MA 02139 (USA), Fax: (+1) 617-324-0253

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Abstract

This report describes a nickel-catalyzed allylic substitution process of simple alkenes whereby an important structural motif, a 1,4-diene, was prepared. The key to success is the use of an appropriate nickel–phosphine complex and a stoichiometric amount of silyl triflate. Reactions of 1-alkyl-substituted alkenes consistently provided 1,1-disubstituted alkenes with high selectivity. Insight into the reaction mechanism as well as miscellaneous application of the developed catalytic process is also documented.

Abstract

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