Highly Selective Activation of Vinyl C–S Bonds Over Aryl C–S Bonds in the Pd‐Catalyzed Coupling of (<i>E</i>)‐(β‐Trifluoromethyl)vinyldiphenylsulfonium Salts: Preparation of Trifluoromethylated Alkenes and Dienes

Abstract

Abstract We describe the Suzuki coupling reaction of ( E )‐(β‐trifluoromethyl)vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl C–S bond is much more favorable (11.7 kcal mol –1 ) than that of the aryl C–S bond.