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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 4: 863 - 870

DOI: https://doi.org/10.6023/cjoc201710025

Articles

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

Received date: 2017-10-22

  Revised date: 2017-11-28

  Online published: 2017-12-08

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.

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Abstract

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

Cite this article

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

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