Synthesis of multisubstituted olefins through regio- and stereoselective silylborylation of an alkynylboronate/chemoselective cross-coupling sequences

Jiao Jiao, Kiyohiko Nakajima, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    38 Citations (Scopus)

    Abstract

    A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-Bpin undergoes a Pd(OAc) 2/tOctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (Z)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.

    Original languageEnglish
    Pages (from-to)3294-3297
    Number of pages4
    JournalOrganic Letters
    Volume15
    Issue number13
    DOIs
    Publication statusPublished - Jul 5 2013

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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