Electrochemical Synthesis of trans-2,3-Disubstituted Aziridines via Oxidative Dehydrogenative Intramolecular C(sp³)-H Amination

Huiqiao Wang, Jianxue Shi, Jiajing Tan*, Wenting Xu, Sheng Zhang* and Kun Xu*

*Beijing University of Chemical Technology, Beijing 100029; Nanyang Normal University, Nanyang 473061, China, Email: tanjjmail.buct.edu.cn; shengzhang@nynu.edu.cn; xukunnynu.edu.cn

H. Wang, J. Shi, J. Tan, W. Xu, S. Zhang, K. Xu, Org. Lett., 2019, 21, 9430-9433.

DOI: 10.1021/acs.orglett.9b03641

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Abstract

An electrochemical oxidative dehydrogenative C(sp³)-H amination reaction for the construction of trans-2,3-disubstituted aziridines avoids the use of external oxidants and generates only hydrogen gas as the byproduct. With KI as the mediator and electrolyte, the desired aziridines were prepared in good yields in an undivided cell at room temperature.

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proposed mechanism

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Key Words

aziridines, electrochemistry

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ID: J54-Y2019