A General Radical Functionalization of Quinoxalin-2(1H)-ones via a Donor–Acceptor Inversion Strategy

Abstract

The radical donor−acceptor inversion strategy represents a highly promising approach in the field of radical chemistry. The present study initially describes a metal-free, versatile, and modular approach for the radical functionalization of quinoxalin-2(1H)-ones via a strategy of radical donor−acceptor inversion under simple reaction conditions. More than 66 examples were provided in moderate yields. The mechanistic study has confirmed that the driving force behind this radical reaction is the in situ formation of a salt through the interaction between quinoxalin-2(1H)-ones and acid/HFIP, which exhibits potent oxidation properties. Additionally, it has been observed that the evident hydrogen bonding between quinoxalin-2(1H)-ones and HFIP can effectively mitigate the oxidation potential.