Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 863-870.DOI: 10.6023/cjoc201710025 Previous Articles     Next Articles

Special Issue: 元素有机化学合辑2018-2019



王清, 高克成, 邹建平, 曾润生   

  1. 苏州大学材料与化学化工学部 苏州 215123
  • 收稿日期:2017-10-22 修回日期:2017-11-28 发布日期:2017-12-08
  • 通讯作者: 曾润生
  • 基金资助:


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

Wang Qing, Gao Kecheng, Zou Jianping, Zeng Runsheng   

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2017-10-22 Revised:2017-11-28 Published:2017-12-08
  • Contact: 10.6023/cjoc201710025
  • Supported by:

    Project 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.

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.

Key words: trifluoromethylation, Togni reagent, catalyst, enamide