Non-metal-mediated N-oxyl radical (TEMPO)-induced acceptorless dehydrogenation of N-heterocycles via electrocatalysis

Literature Information

Publication Date 2022-02-16
DOI 10.1039/D1RA08919F
Impact Factor 3.361
Authors

Huiqing Hou, Xinhua Ma, Yaling Ye, Mei Wu, Sunjie Shi, Wenhe Zheng, Mei Lin, Weiming Sun, Fang Ke


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Abstract

The development of protocols for direct catalytic acceptorless dehydrogenation of N-heterocycles with metal-free catalysts holds the key to difficulties in green and sustainable chemistry. Herein, an N-oxyl radical (TEMPO) acting as an oxidant in combination with electrochemistry is used as a synthesis system under neutral conditions to produce N-heterocycles such as benzimidazole and quinazolinone. The key feature of this protocol is the utilization of the TEMPO system as an inexpensive and easy to handle radical surrogate that can effectively promote the dehydrogenation reaction. Mechanistic studies also suggest that oxidative TEMPOs redox catalytic cycle participates in the dehydrogenation of 2,3-dihydro heteroarenes.

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