Schmink JR1, Dockrey SA1, Zhang T1, Chebet N1, van Venrooy A1, Sexton M1, Lew SI1, Chou S1, Okazaki A1.
Org Lett. 2016 Dec 16;18(24):6360-6363. Epub 2016 Dec 1.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 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.