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Updated: May 30, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Electrochemically Driven Ugi-Azide Reaction via C(sp3)-H Bond Activation of Tertiary Amines
Bin Song1, Feng Zhao1, Pengxiang Gao1
1School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China.
Abstract:
An electrochemically driven Ugi-azide reaction was established via C(sp3)-H bond activation of tertiary amines to prepare α-aminomethyl tetrazoles within 2.5 h under mild conditions with remarkable tolerance of various functional groups. Besides, this electrochemical strategy not only obviated the needs of iodine, metal, and exogenous oxidant but possessed potential applicability of convenient large-scale synthesis. Mechanistic studies indicated both the alkyl carbon-centered radical generated at the anode and intramolecular [3 + 2] cycloaddition are key factors for this strategy.
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