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The first Pd-catalyzed Mizoroki-Heck-type reaction of Ph2SRfnOTf with alkenes is described. The reaction of Ph2SRfnOTf (Rfn = CF3, CH2CF3) with alkenes in the presence of 10 mol% PdP(t-Bu)32 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 Ph2SRfnOTf, 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.
Wang et al. (Fri,) studied this question.