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Issue 80, 2016
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Palladium-catalyzed Mizoroki–Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

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Abstract

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

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

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Article information


Submitted
23 Jul 2016
Accepted
23 Aug 2016
First published
25 Aug 2016

Chem. Commun., 2016,52, 11893-11896
Article type
Communication

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

S. Wang, H. Song, X. Wang, N. Liu, H. Qin and C. Zhang, Chem. Commun., 2016, 52, 11893
DOI: 10.1039/C6CC06089G

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