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Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydro-Dehalogenation Reaction
preprintsubmitted on 19.03.2020, 06:44 and posted on 19.03.2020, 12:09 by Alena Vasquez, John Gurak, Candice Joe, Emily Cherney, Keary Engle
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 an [PdII(Ar)(H)] intermediate, which performs selective hydride insertion into the β-position of α,β-unsaturated carbonyl compounds.