Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Addition of Interelement Compounds Having B–Si, B–B, and Cl–S Bonds to Alkynes, and Subsequent Cross-Couplings

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Abstract

Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups. (Figure presented.).

Original languageEnglish
Pages (from-to)2031-2045
Number of pages15
JournalChemical Record
DOIs
Publication statusPublished - Aug 1 2016
Externally publishedYes

Keywords

  • alkynes
  • chlorothiolation
  • cross-coupling
  • diborylation
  • silaboration

ASJC Scopus subject areas

  • Biochemistry
  • Chemistry(all)
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

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