Palladium-catalyzed Mizoroki–Heck-type reactions of [Ph₂SR_fn][OTf] with alkenes at room temperature

Abstract

The first Pd-catalyzed Mizoroki-Heck-type reaction of [Ph₂SR_fn][OTf] with alkenes is described. The reaction of [Ph₂SR_fn][OTf] (R_fn = CF₃, CH₂CF₃) with alkenes in the presence of 10 mol% Pd[P(t-Bu)₃]₂ and TsOH at room temperature provided the corresponding phenylation products in good to high yields. The bases that benefit the traditional Mizoroki-Heck reactions severely inhibited the transformation with [Ph₂SR_fn][OTf], whereas acids significantly improved the reaction. This protocol supplies a new class of cross-coupling partners for Mizoroki-Heck-type reactions and gains important insights into the reactivity of phenylsulfonium salts either with or without fluorine-containing alkyl groups as the promising phenylation reagents in organic synthesis.