Work

Direct Aroylation of Olefins through a Cobalt/Photoredox‐Catalyzed Decarboxylative and Dehydrogenative Coupling with α‐Oxo Acids

Year: 2022

Type: article

Abstract: A photoredox/cobalt dual catalytic procedure has been developed that allows benzoylation of olefins. Here the photoredox catalyst effects the decarboxylation of α-ketoacids to form benzoyl radicals. After addition of this radical to styrenes, the cobalt catalyst abstracts a H-atom. Hydrogen evolution from the putative cobalt hydride intermediate allows a Heck-like aroylation without the need for a stoichiometric oxidant. Mechanistic studies reveal that electronically different styrenes lead to a curved Hammett plot, thus suggesting a change in product-determining step in the catalytic mechanism.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202202781

Authors: Alex M. Davies, Rafael D. Hernandez, Jon A. Tunge

Institution: University of Kansas

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Division of Chemistry

Awards: G3143887096, G889195605