Divergent Auto‐oxidative Alkylation and Alkanoacylation of Quinoxalin‐2(1H)‐ones with Aliphatic Aldehydes

Abstract

Auto-oxidation of aliphatic aldehydes generates alkyl radicals and alkanoyl radicals, which can be intercepted to generate carbon-carbon bonds. However, the highly reactive and unstable radical intermediates make the controlling selectivity alkylation and alkanoacylation especially challenging. Herein, we report a sustainable and controllable protocol for the auto-oxidative alkylation and alkanoacylation of quinoxalin-2(1H)-ones with good reactivity and selectivity. This protocol was presented in a green and sustainable manner, using oxygen as the only oxidant, avoiding the use of catalysts and explosive oxidants. It offers a new paradigm for a convenient, green synthesis of alkyl and alkanoyl compounds from abundant aliphatic aldehydes.