Selective synthesis of multisubstituted olefins utilizing gem - And vic -diborylated vinylsilanes prepared by silylborylation of an alkynylboronate and diborylation of alkynylsilanes

Jiao Jiao, Keita Hyodo, Hao Hu, Kiyohiko Nakajima, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    45 Citations (Scopus)

    Abstract

    The synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.

    Original languageEnglish
    Pages (from-to)285-295
    Number of pages11
    JournalJournal of Organic Chemistry
    Volume79
    Issue number1
    DOIs
    Publication statusPublished - Jan 3 2014

    ASJC Scopus subject areas

    • Organic Chemistry

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