Authors: Schmink, JR; Dockrey, SAB; Zhang, TY; Chebet, N; van Venrooy, A; Sexton, M; Lew, SI; Chou, S; Okazaki, A
ORGANIC LETTERS, 18 (24):6360-6363; 10.1021/acs.orglett.6b03249 DEC 16 2016
A nontraditional approach to synthesizing aryl vinyl sulfides is described. 2,2-Diphenyl-1,3-oxathiolane slowly liberates a 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 Pd /PdIl 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.