The palladium-catalyzed, alpha-selective hydroarylation of acrylates and acrylamides is reported. Under optimized conditions, this method is highly tolerant of a wide range of substrates including those with base sensitive functional groups and/or multiple enolizable carbonyl groups. A detailed mechanistic study was undertaken, and the high selectivity of this transformation was shown to be enabled by the formation of a [Pd-II(Ar)(H)] intermediate, which performs selective hydride insertion into the beta-position of alpha,beta-unsaturated carbonyl compounds.