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 journalArticle

35 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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