Copper-Catalyzed Alkylation of Quinoxalin-2(1H)-ones with Styrenes and tert-Butyl Peroxybenzoate

Abstract

A simple strategy for the synthesis of 3-substituted Quinoxalin-2(1H)-ones containing ether units is proposed. The method is realized by the three-component synthesis of Quinoxalin-2(1H)-ones, styrenes and tert-Butyl peroxybenzoate (TBPB). This reaction has good functional group tolerance and may involve a free radical process.

Recent Developments in Direct C–H Functionalization of Quinoxalin-2(1H)-Ones via Multi-Component Tandem Reactions

“…In 2021, Yao et al [ 45 ] described a metal-free catalytic, H 2 O 2 -mediated three-component reaction of quinoxalin-2(1 H )-ones, DMSO and styrene. A series of 3-substituted quinoxalin-2(1 H )-ones were synthesized using DMSO as the methylation reagent ( Scheme 13 ).…”

“…In 2022, Yao et al [ 49 ] implemented a simple strategy for the synthesis of 3-substituted quinoxalin-2(1 H )-ones containing ether units via a three-component synthesis of quinoxalin-2(1 H )-one, styrene, and tert-butyl peroxybenzoate (TBPB) using CuCl as a catalyst ( Scheme 16 ). This method introduced both C–C and C–O bonds in the product with acceptable functional group tolerance.…”

Three‐Component Reactions of Quinoxalin‐2(1H)‐ones: Recent Advances

“…In 2022, Lin and coworkers [50] employed a novel three‐component strategy to construct C−C and C−O bonds via the reaction of quinoxalin‐2(1 H )‐one, styrene, and tert‐butyl peroxybenzoate (TBPB) by using CuCl as a catalyst, showing good tolerance for functional groups (Scheme 33). According to the proposed mechanism, upon heating, benzoyloxy radicals and tert‐butoxy radicals were produced via the homolytic cleavage of TBPB.…”