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Decarboxylative Allylation of Trifluoroethyl Sulfones and Approach to Difluoromethyl Compounds

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journal contribution
posted on 2012-10-19, 00:00 authored by Norio Shibata, Kazunobu Fukushi, Tatsuya Furukawa, Satoru Suzuki, Etsuko Tokunaga, Dominique Cahard
Allyl carbonates undergo palladium-catalyzed decarboxylative allylation of trifluoroethyl phenyl sulfones. The success of the allylation, which is not efficient under typical strong base-mediated conditions, is the result of mild conditions thanks to a progressive delivery of ethoxide. Indeed, ethyl allyl carbonates act as a latent source of ethoxide for generation of the trifluoroethyl carbanion that reacts with the π-allylpalladium complex. The utility of the method is illustrated in a new approach to difluoromethyl compounds.

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