Electrochemically Enabled [3 + 2] Cycloaddition of Alkenes with Vinyl Azides: Direct Access to 2,4,5-Trisubstituted
Shaoxiong Yang1, Yanren Zhu1, Enfan Pu1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education; Yunnan Key Laboratory of Cross-Border Infectious Disease Control and Prevention and Novel Drug Development, Yunnan Provincial Center for Research & Development of Natural Products; School of Chemical Science and Technology; School of Pharmacy, Yunnan University, Kunming 650500, China.
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.
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