Anode material determined divergent 5-exo-dig cyclization of N-cyano-2-halobenzamides toward 3-iminoisoindolin-1-ones and 3-aminoisoindolin-1-ones

Abstract

Herein, an electroreductive aryl radical enabled 5-exo-dig cyclization of N-cyano-2-halobenzamides is presented, providing a convenient route for the synthesis of a variety of 3-iminoisoindolin-1-ones in 30–75% yields. Simply by employing zinc plate instead of graphite rod anode, the products of the electrosynthesis are switched to diverse 3-aminoisoindolin-1-ones through aryl-radical-mediated 5-exo-dig cyclization and subsequent reductive hydrogenation. Furthermore, this anode material determined divergent 5-exo-dig cyclization features mild electrochemical conditions, excellent substrate scopes, and good functional group tolerance.