Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction.

Alena M Vasquez, John A Gurak, Candice L Joe, Emily C Cherney, Keary M Engle

Journal of the American Chemical Society 2020 Jun 10

filter terms:

The palladium-catalyzed, α-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 [PdII(Ar)(H)] intermediate, which performs selective hydride insertion into the β-position of α,β-unsaturated carbonyl compounds.

Citation

Alena M Vasquez, John A Gurak, Candice L Joe, Emily C Cherney, Keary M Engle. Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction. Journal of the American Chemical Society. 2020 Jun 10;142(23):10477-10484