Negishi Coupling between α-Alkyl(aryl)thio Vinyl Zinc Chloride and α-Bromo Vinyl Ether: A Convergent Synthesis of 2-Alkoxy-3-alkyl(aryl)thiobuta-1,3-dienes¹

Abstract

[reaction: see text] A convergent approach for the stereoselective synthesis of 2-alkoxy-3-alkyl(aryl)thiobuta-1,3-dienes has been developed. It was found that Negishi coupling between alpha-alkyl(aryl)thio vinyl zinc chloride and alpha-bromo vinyl ether or Negishi coupling between alpha-bromo vinyl sulfide and alpha-alkoxy vinyl zinc chloride provided the best yield and stereoselectivity.