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Updated: May 1, 2026

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Copper-Catalyzed Intermolecular Trifluoromethylazidation of Allenamides: An Access to CF3-Containing (E)-Allyl Azides
Jiri Gele1, Xingyao She1, Jiang Wang1
1Key Laboratory of Basic Chemistry of the State Ethnic Commission, School of Chemistry and Environment, Southwest Minzu University, Chengdu 610041, P. R. China.
Abstract:
A mild and efficient method for copper-catalyzed intermolecular trifluoromethylazidation of allenamides was explored. This method is effective for a broad range of allenamides and it facilitates efficient synthesis of a wide variety of CF3-containing (E)-allyl azides, which can be used for further transformation to amine and triazole derivatives. Mechanistic investigations indicated that a (E)-CF3-allyl radical Int I was first formed via the CF3 radical added to the central carbon of allenamides. The stereocontrol on the alkene is may be realized via the steric hindrance of the amine and CF3 group. The CF3-allyl radical species Int I subsequently combined with Cu(II)/N3- to give a CF3-allyl-Cu(III) species Int II, which underwent reductive elimination to furnish the final product 2.
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