K2S2O8 mediated C-3 arylation of quinoxalin-2(1H)-ones under metal-, photocatalyst- and light-free conditions

Abstract

Two facile and effective C-3 arylation protocols of quinoxalin-2(1H)-ones with arylhydrazines and aryl boronic acids respectively via free radical cross-coupling reactions under metal-, photocatalyst- and light-free conditions have been unveiled. K₂S₂O₈ has been used as an efficient oxidant to generate aryl radicals from arylhydrazines and aryl boronic acids under two different reaction conditions. The generated aryl radicals undergo a free radical coupling reaction at the C-3 position of quinoxalin-2(1H)-ones producing 3-arylquinoxalin-2(1H)-ones in good to excellent yields. The involvement of radicals in the course of the reaction has been demonstrated by radical trapping experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl.