Electrochemically Enabled [3 + 2] Cycloaddition of Alkenes with Vinyl Azides: Direct Access to 2,4,5-Trisubstituted 1-Pyrrolines

Organic Letters 2026

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Authors: Shaoxiong Yang, Yanren Zhu, Enfan Pu, Menghua Chen, Silei Ye, Piaopiao Jiang, Xiong Li, Hongbin Zhang, Jingbo Chen
DOI: 10.1021/acs.orglett.5c04941
Cited by: 1
References: 63

Abstract

Electrosynthesis provides an efficient route for the construction of heterocyclic compounds. Herein, we report an electrochemically promoted [3 + 2] cycloaddition of alkenes with vinyl azides under mild conditions. This strategy enables the direct synthesis of 2,4,5-trisubstituted-1-pyrrolines. Compared with conventional methods, this approach requires no oxidants, reductants, or metals. Mechanistic studies have revealed that the reaction proceeds via a cyclization process of alkene radical cations, and both the anode and the cathode play indispensable roles in the reaction.

Fields of Study & Subjects

Radical Photochemical Reactions CO2 Reduction Techniques and Catalysts Cyclopropane Reaction Mechanisms

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
4
Pages
1214–1220
Publication date
21 January 2026
Language
EN