Photochemical organocatalytic heteroarylation of anilines and secondary alicyclic amines in continuous-flow

C-N bond formation plays a crucial role in various chemical synthesis processes in both the chemical industry and nature. While numerous methods have been developed for the formation of C-N bonds, only a few meet the criteria of "green chemistry". In this study, we present a continuous-flow procedure for the decyanative N-heteroarylation of anilines and secondary alicyclic amines using a photoorganocatalytic reaction. Through the synergistic combination of photochemistry, organocatalysis, and continuous-flow technology, we were able to achieve high and close to quantitative yields, while significantly reducing the reaction time from 12 hours in batch procedures to just 1 hour in continuous-flow conditions. Photoorganocatalytic arylation of amines in continuous-flow enables scaling up including decreasing of both reaction time and catalyst loading.