Mild and Functional Group-Tolerant Aerobic <i>N</i>-Dealkylation of Tertiary Amines Promoted by Photoredox Catalysis

This article describesthe development of a mild methodfor the N-dealkylation of tertiary amines via photoredoxcatalysisand its application in late-stage functionalization. Using the developedmethod, more than 30 diverse aliphatic, aniline-type, and complexsubstrates are shown to undergo N-dealkylation, providinga method with broader functional group tolerance compared to methodsfound in the literature. The scope also includes tertiary and secondaryamine molecules with complex substructures and drug substrates. Interestingly,alpha-oxidation to imines was observed in several cyclic substructuresinstead of N-dealkylation, suggesting that iminesare relevant reaction intermediates.