Citation: Wang Qing, Gao Kecheng, Zou Jianping, Zeng Runsheng. Copper(I)-Catalyzed Non-terminal Enamides Trifluoromethylation: Flexible Synthesis of N-(3, 3, 3-Trifluoro-2-arylprop-1-en-1-yl) Substituted Benzamide[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 863-870. doi: 10.6023/cjoc201710025 shu

Copper(I)-Catalyzed Non-terminal Enamides Trifluoromethylation: Flexible Synthesis of N-(3, 3, 3-Trifluoro-2-arylprop-1-en-1-yl) Substituted Benzamide

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Corresponding author: Zeng Runsheng, zengrunsheng@suda.edu.cn
Received Date: 22 October 2017
Revised Date: 28 November 2017
Available Online: 8 April 2017
Fund Project: the National Natural Science Foundation of China 21472133the Prospective Study Program of Jiangsu Province BY2015039-08Project supported by the Prospective Study Program of Jiangsu Province (No. BY2015039-08), the National Natural Science Foundation of China (No. 21472133) and the Priority Academic Program Development of Jiangsu Higher Education Institutions

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A novel CuI-catalyzed trifluoromethylation of non-terminal enamides was investigated. N-Arylvinyl-substituted benzamide reacted with Togni reagent in dichloroethylane to afford N-(3, 3, 3-trifluoro-2-arylprop-1-en-1-yl) substituted benzamide. The reaction proceeded at 90℃ in air atmosphere in the presence of base and ligands. Control experiment shows that the Togni reagent firstly released CF₃ radical in the presence of copper(I) salts and CF₃ radical selectively added to the carbon-carbon double bond of β-position of enamides.
- trifluoromethylation,
- Togni reagent,
- catalyst,
- enamide
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