Liu Dan, Patureau Frederic W
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.
Org Lett. 2024 Aug 16;26(32):6841-6846. doi: 10.1021/acs.orglett.4c02316. Epub 2024 Aug 7.
A visible-light-induced photocatalytic deoxygenative benzylation of quinoxalin-2-(1)-ones is herein described. This novel approach provides a mild, simple, and practical route to 3-benzylquinoxalin-2(1)-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(1)-ones with great potential for valuable applications in drug discovery. Mechanistic investigations suggest HO as a proton source, while hydroxyl-containing quinoxalin-2(1)-ones may be key intermediates of the photocatalytic deoxygenative process.