Citation: Yang Lifeng, Hui Renjie, Shan Hengyue, Gong Kai. Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3242-3247. doi: 10.6023/cjoc201711015 shu

Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles

School of Pharmaceutical Science, Jiangnan University, Wuxi 214122

Corresponding author: Gong Kai, gongkai@jiangnan.edu.cn
Received Date: 8 November 2017
Revised Date: 4 December 2017
Available Online: 8 December 2017
Fund Project: the National Natural Science Foundation of China 51303069the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions PPZY2015B146Project supported by the National Natural Science Foundation of China (No. 51303069), and the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions (No. PPZY2015B146)

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Since benzimidazole containing moieties have a lot of pharmacological activities, we reported the ageneral metal-free and cost-effective, I₂/DTBP-catalyzed method for the functionalization of N-H bonds of azoles via α-C(sp³)-H activation of cyclic ethers or cyclic thioethers. And this method is also applicable to a diverse range of N-substituted azoles and cyclic ethers/thioethers. By using the free-radical scavenger 2, 2, 6, 6-tetramethylpiperidin-1-oxyl (TEMPO) as a control, we suggest that a radical/SET mechanism proceeding via a radical/oxonium or thionium ion may be involved in the reaction.
- iodine,
- functionalization of N-H bond,
- cyclic ether,
- cross dehydrogenative coupling,
- cyclic thioether
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