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Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydro-Dehalogenation Reaction

preprint
submitted on 19.03.2020 and posted on 19.03.2020 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.

Funding

NIH-5R35GM125052-03

NIH-5R35GM125052-03S1

NSF-DGE-1346837

Alfred P. Sloan Fellowship

Camille Dreyfus Teacher-Scholar Program

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

Exports