Metal-free site-selective C–H cyanoalkylation of 8-aminoquinoline and aniline-derived amides with azobisisobutyronitrile

Using K₂S₂O₈, an efficient and metal-free site-selective C–H cyanoalkylation of 8-aminoquinoline and aniline-derived amides with AIBN (azobisisobutyronitrile) was developed. Without any catalyst, various substrates and functional groups were compatible to afford corresponding products in moderate to high yields. A mechanism study displayed that a radical–radical coupling process was involved via the N-centered radical generation and delocalization of aryl amides.

An efficient metal-free cyanoalkylation of 8-aminoquinoline and aniline-derived amides was achieved in the presence of K₂S₂O₈. The method showed good substrate tolerance and also suitable for bromination and dimerization reactions.