A Domino Azidation/C-H Amination Approach toward Trifluoromethyl Substituted Imidazoles

Haichao Ma, Xiaoyan Zhang, Liangliang Chen and Wei Yu*

*State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China, Email: yuweilzu.edu.cn

H. Ma, X. Zhang, L. Chen, W. Yu, J. Org. Chem., 2017, 82, 11841-11847.

DOI: 10.1021/acs.joc.7b01361

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Abstract

N-Alkyl enamines can be transformed into highly subsituted imidazoles in the presence of (diacetoxyiodo)benzene and TMSN₃ under catalysis of a copper salt such as Cu(OAc)₂ via a domino azidation/intramolecular C(sp³)-H amination. The present reaction provides an efficient method for the preparation of 4-(trifluoromethyl) imidazoles.

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Key Words

imidazoles, (diacetoxyiodo)benzene

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ID: J42-Y2017