alpha-Arylsulfonyloxyacrylates: attractive O-centered electrophiles for synthesis of alpha-substituted acrylates via Pd-catalysed Suzuki reactions

We herein report alpha-arylsulfonyloxyacrylates as a kind of useful and attractive O-centered electrophiles for Suzuki cross-coupling reactions. A range of alpha-(hetero)aryl substituted acrylates has been prepared via the palladium-catalysed C-C cross-coupling reactions between potassium (hetero)aryltrifluoroborates and alpha-arylsulfonyloxyacrylates. Moreover, alpha-arylsulfonyloxyacrylate could also react with B-alkyl-9-BBN to produce alpha-alkyl substituted acrylates. The synthetic application of this new method was demonstrated by the preparation of the intermediate for synthesis of retinoid X receptors-selective retinoids. These Suzuki reaction-based protocols feature broad substrate scope, generality, and mild reaction conditions.