This article describes
the development of a mild method
for theN-dealkylation of tertiary amines via photoredox
catalysis
and its application in late-stage functionalization. Using the developed
method, more than 30 diverse aliphatic, aniline-type, and complex
substrates are shown to undergoN-dealkylation, providing
a method with broader functional group tolerance compared to methods
found in the literature. The scope also includes tertiary and secondary
amine molecules with complex substructures and drug substrates. Interestingly,
α-oxidation to imines was observed in several cyclic substructures
instead ofN-dealkylation, suggesting that imines
are relevant reaction intermediates.