C–H Imidation and Dual C–H Bond Aminobromination of Five-Membered Heterocycles

Here, we report a practical C–H imidation of five-membered heterocycles under metal-free conditions. We also report the first dual C–H bond aminobromination of thiophenes, with benzotriazole, saccharin, 1,2,4-triazole, benzimidazole, pyrazole, 4-bromopyrazole, 5-methyltetrazole, and dibenzenesulfonimides as effective amine sources. Mechanistic studies support the radical pathway of the imidation and aminobromination reactions.