Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines

The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddition reaction of N-nitrosoamines to alkenes was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines to telescope the direct handling of harmful N-nitroso compounds, where the desired aamino oxime derivatives were obtained in a one-pot tandem Nnitrosation and photoaddition sequence.

Automated summary

The study for the first time disclosed the generation of aminium radical cation species from N-nitrosoamines through visible-light excitation at 453 nm, and achieved the photoaddition reaction of N-nitrosoamines to alkenes. By combining the aerobic oxidation protocol of amines, the one-pot synthesis of aamino oxime derivatives was successfully realized in a tandem N-nitrosation and photoaddition sequence.