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

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

Sun, Kai;Li, Yali;Feng, Ranran;Mu, Shiqiang;Wang, Xin;Zhang, Bing;
The Journal of organic chemistry 2020 Vol. 85 pp. 1001-1008
263
sun2020chthe

Abstract

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.

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81878
Unique Identifier:
10.1021/acs.joc.9b02941
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