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

doi:10.6023/cjoc201710025

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

Articles

铜(I)催化的非末端烯酰胺的三氟甲基化反应:N-(3,3,3-三氟-2-芳基-1-丙烯基)取代苯甲酰胺的合成

王清, 高克成, 邹建平, 曾润生

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 E-mail:zengrunsheng@suda.edu.cn
基金资助:
江苏省产学研前瞻性联合研究（No.BY2015039-08）、国家自然科学基金（No.21472133）、江苏省高等学校优势学科基金资助项目.

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

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 E-mail:zengrunsheng@suda.edu.cn
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.

1. Copper(I)-Catalyzed Non-terminal Enamides Trifluoromethylation: Flexible Synthesis of N-(3,3,3-Trifluoro-2-arylprop-1-en-1-yl) Substituted Benzamide.PDF(1870KB)

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

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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]. Chin. J. Org. Chem., 2018, 38(4): 863-870.

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铜(I)催化的非末端烯酰胺的三氟甲基化反应:N-(3,3,3-三氟-2-芳基-1-丙烯基)取代苯甲酰胺的合成

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

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