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 journalArticle

40 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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