Metal-Free Addition of Alkyl Bromides to Access 3,3-Disubstituted Quinoxalinones Enabled by Visible-Light Photoredox Catalysis
- Jennie Liaoa, David N. Hunterb, Ugochinyere Nancy Oloyedeb, Joseph W. McLaughlinb, Cheng Wangb, and Abdellatif El Marrounib
- aProcess Research & Development, MRL, Merck & Co., Inc., West Point, Pennsylvania 19486, United States
- bDiscovery Chemistry, MRL, Merck & Co., Inc., West Point, Pennsylvania 19486, United StatesRead the publication that featured this abstract
A metal-free addition of unactivated alkyl bromides to quinoxalin-2(1H)-ones is described. This method enables the construction of valuable 3,3-disubstituted dihydroquinoxalin-2(1H)-ones bearing quaternary carbon centers under mild, visible-light photoredox catalysis. High functional group tolerance is observed in both the quinoxalinone and alkyl bromide partners. The ability to scale up this method was demonstrated under photo-flow conditions to enable gram-scale synthesis.
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