Regioselective electrochemical 7-endo-dig selenocyclization of N-benzyl propiolamides to access selenated benzo[c]azepinones

Abstract

An electrochemical approach for regioselective 7-endo-dig selenocyclization of N-benzyl propiolamides with diselenides has been developed. This methodology circumvents the need for metal reagents or oxidants, thereby exhibiting excellent functional group tolerance and substrate compatibility. A diverse array of selenated benzo[c]azepinones can be obtained with good to excellent regioselectivity and yields. Furthermore, gram-scale synthesis and subsequent transformations of the products can be readily achieved under straightforward experimental protocols.