A non-traditional approach to synthesizing aryl vinyl sulfides is described. 2,2-diphenyl-1,3-oxathiolane slowly liberates vinyl sulfide anion under basic conditions. Using a Pd/Xantphos catalyst system to activate a wide range of aryl bromides, this transient sulfide species can be effectively trapped and fed into a traditional Pd0/PdII catalytic cycle. Scope and limitations of the methodology are presented along with significant discussion of a competitive C–S bond activation by this catalyst system.

A non-traditional approach to synthesizing aryl vinyl sulfides is described. 2,2-diphenyl-1,3-oxathiolane slowly liberates vinyl sulfide anion under basic conditions. Using a Pd/Xantphos catalyst system to activate a wide range of aryl bromides, this transient sulfide species can be effectively trapped and fed into a traditional Pd0/PdII catalytic cycle. Scope and limitations of the methodology are presented along with significant discussion of a competitive C–S bond activation by this catalyst system