Selective Oxidative Methyl C–H Functionalization of Butylated Hydroxytoluene toward Arylimines/N-Heterocycles

A metal-free and selective oxidative methyl C–H functionalization of BHT with aniline compounds has been developed. This innovative method enables the facile and efficient synthesis of a diverse array of BHT-functionalized N-containing skeletons, including arylamines, benzoxazoles, benzothiazoles, benzimidazoles, quinazolines, and quinazolinones, all of which are challenging to access. The control experiment involving TEMP18O suggests that the radical adduct of TEMPO with the benzyl radical of BHT may serve as an intermediate.