American Chemical Society
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Oxidative Addition of Pd(0) to Ar−SO2R Bonds:  Heck-Type Reactions of Sulfones

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journal contribution
posted on 2006-06-22, 00:00 authored by José Luis García Ruano, José Alemán, Cristina García Paredes
Phenyl vinyl sulfones and sulfoxides react with Pd(OAc)2 to form styryl sulfoxides and sulfones according to the first Mizoroki−Heck reaction reported for these thio derivatives. Only sulfones are able to react by using catalytic amounts of Pd (up to 1 mol %) in the presence of Ag2CO3. 1,2-Diphenylsulfonyl ethenes, alkynylphenyl sulfones, and other sulfones, less prone to act as acceptors in the Heck-type reactions, can transfer the aryl group to alkyl acrylates forming cinnamic esters.