Work

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

Year: 2020

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.0c03040

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

Institutions: Scripps Research Institute, Bristol-Myers Squibb (United States), Bristol-Myers Squibb (United Kingdom)

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institute of General Medical Sciences

Awards: Combinatorial, Catalytic Functionalization of Alkenes and Alkynes, Graduate Research Fellowship Program (GRFP)