Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

A Domino Azidation/C–H Amination Approach toward Trifluoromethyl Substituted Imidazoles
Liangliang Chen, Haichao Ma, Wei Yu, Xiaoyan Zhang
N-Alkyl enamines can be transformed into 2,4,5-trisubsituted imidazoles by reacting with (diacetoxyiodo)benzene and TMSN3 under the catalysis of a copper salt such as Cu(OAc)2. Tetrabutyl ammonium iodide was also capable of promoting the reaction. The transformation from N-alkyl enamines into 2,4,5-trisubsituted imidazoles took place in a domino azidation/intramolecular C(sp3)–H amination pattern. The present reaction provides a new efficient method for the preparation of 4-(trifluoromethyl) imidazoles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01361

DOI: 10.1021/acs.joc.7b01361

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