Electrochemical vicinal amidoselenation of unactivated olefins via a tandem Ritter reaction

Abstract

A straightforward strategy for the electrochemical vicinal amidoselenation of unactivated olefins via a tandem Ritter reaction was developed. The reaction was carried out with diaryl diselenides as selenylation reagents and acetonitrile as a nucleophile. Various amidoselenation products can be afforded from unactivated olefins under mild and metal- and oxidant-free electrochemical conditions. This strategy features a broad substrate scope, good functional group tolerance, scale-up synthesis, simple operation and mild reaction conditions. Detailed mechanistic insights and DFT calculations provided strong support for the tandem radical selenylation/oxidative Ritter reaction.