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.