Anode material determined divergent 5‐<i>exo</i>‐<i>dig</i> cyclization of <i>N</i>‐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.