Borylstannylation of alkynes with inverse regioselectivity: copper-catalyzed three-component coupling using a masked diboron

Chem Commun (Camb). 2015 Apr 14;51(29):6297-300. doi: 10.1039/c5cc00439j.

Abstract

A variety of terminal alkynes are facilely convertible into cis-boryl(stannyl)alkenes with inverse regioselectivity to those of the previous borylstannylation by the copper-catalyzed three-component reaction using a masked diboron. The synthetic utility of the resulting boryl(stannyl)alkenes has been demonstrated by chemoselective coupling reactions.

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Boron / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Copper
  • Boron