4.7 Article

Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

期刊

CHEMICAL COMMUNICATIONS
卷 52, 期 80, 页码 11893-11896

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc06089g

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资金

  1. University of Technology
  2. Natural Science Foundation of Hubei Province (China) [2015CFB176]
  3. Chutian Scholar Program from Department of Education of Hubei Province (China)
  4. Hundred Talent Program of Hubei Province

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The first Pd-catalyzed Mizoroki-Heck-type reaction of [Ph2SRfn][OTf] with alkenes is described. The reaction of [Ph2SRfn][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 [Ph2SRfn][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.

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