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.