Visible-Light-Induced Photocatalytic Deoxygenative Benzylation of Quinoxalin-2-(1 H)-ones with Carboxylic Acid Anhydrides

Org Lett. 2024 Aug 16;26(32):6841-6846. doi: 10.1021/acs.orglett.4c02316. Epub 2024 Aug 7.

Abstract

A visible-light-induced photocatalytic deoxygenative benzylation of quinoxalin-2-(1H)-ones is herein described. This novel approach provides a mild, simple, and practical route to 3-benzylquinoxalin-2(1H)-ones from ubiquitous and safe carboxylic acid anhydrides. A wide range of substrates with different substituents were well-tolerated and efficiently transformed to various functionalized 3-benzylquinoxalin-2(1H)-ones with great potential for valuable applications in drug discovery. Mechanistic investigations suggest H2O as a proton source, while hydroxyl-containing quinoxalin-2(1H)-ones may be key intermediates of the photocatalytic deoxygenative process.