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Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy

Yang Yu, Meijuan Li, Yong Zhang, Yonghai Liu, Lei Shi, Wei Wang*, Hao Li*

*University of Arizona, Tucson, Arizona 85721-0207, United States; East China University of Science and Technology, Shanghai 200237, China Email: wwangpharmacy.arizona.edu, hli77ecust.edu.cn

Y.-D. Du, Z.-J. Xu, C.-Y. Zhou, C.-M. Che, Org. Lett., 2019, 21, 895-899.

DOI: 10.1021/acs.orglett.8b03799 (free Supporting Information)


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Abstract

A copper-promoted intramolecular C-H oxidative amination reaction between secondary amine (N-H) and C(sp3)-H at the benzylic position of azaarenes or α-position of ketones enables the synthesis of aziridine derivatives in the presence of oxygen as sole oxidant. Moreover, a Yb(OTf)3-CuI relay system catalyzes the aziridination of electron-deficient vinylarenes with unprotected primary alkyl amines.


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Key Words

aziridines, oxygen


ID: J54-Y2019