Electrosynthesis of a cyclo-N5− anion via TEMPO-mediated selective C–N bond cleavage in aryl-pentazole

Feng Zhao; Ziyan Gu; Bin Song; Xuehai Ju; Bingcheng Hu; Chong Zhang

doi:10.1039/D5CC02899J

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Electrosynthesis of a cyclo-N₅⁻ anion via TEMPO-mediated selective C–N bond cleavage in aryl-pentazole†

Feng Zhao,‡^a Ziyan Gu,‡^a Bin Song,^a Xuehai Ju,

^a Bingcheng Hu

*^a and Chong Zhang

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, China
E-mail: hubc@njust.edu.cn, czhang@njust.edu.cn

Abstract

A non-metal and efficient electrochemical strategy for synthesizing a cyclo-N₅⁻ anion through TEMPO-catalysed selective C–N bond cleavage in aryl-pentazole has been established. This novel protocol features avoidance of metal catalysts, mild conditions, water as the sole oxygen source, and applicability to other N-arylzoles.

This article is part of the themed collection: Chemical Communications HOT articles 2025

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Article information

DOI: https://doi.org/10.1039/D5CC02899J
Article type: Communication
Submitted: 22 May 2025
Accepted: 21 Jul 2025
First published: 22 Jul 2025

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Chem. Commun., 2025, Advance Article

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Electrosynthesis of a cyclo-N₅⁻ anion via TEMPO-mediated selective C–N bond cleavage in aryl-pentazole

F. Zhao, Z. Gu, B. Song, X. Ju, B. Hu and C. Zhang, Chem. Commun., 2025, Advance Article , DOI: 10.1039/D5CC02899J

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