Catalytic and non-catalytic selective aryl transfer from (mesityl)iodonium(III) salts to diarylsulfide compounds

Abstract

We report a facile synthesis of triarylsulfonium triflates by selective aryl transfer from readily available mesityl iodonium(III) salts to diarylsulfides in the presence of a copper catalyst. The advantage of our protocol is that the iodonium(III) salts bearing a mesitylene (Mes) auxiliary efficiently promote selective S-arylation of diarylsulfides to produce the desired triarylsulfonium triflates without the formation of Mes-derived byproduct salts.

Selective S-arylation of thiols with o-OTf-substituted diaryliodonium salts toward diarylsulfides

“…2 In the past few years, hypervalent iodine reagents have proven to be practical and efficient tools for C–S bond formation under mild conditions. 3 The coupling reactions of diaryliodonium salts with thiols proceeded smoothly to afford aryl sulfides in an experimentally simple manner (Scheme 1a). 4 In 2014, Ding reported a base-mediated S -arylation for the synthesis of aryl sulfides with diaryliodonium salts in good yields.…”