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Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Xinqiang Tan, Zhonglin Liu, Haigen Shen, Pei Zhang, Zhenzhen Zhang and Chaozhong Li*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: cligmail.sioc.ac.cn

X. Tan, Z. Liu, H. Shen, P. Zhang, Z. Zhang, C. Li, J. Am. Chem. Soc., 2017, 139, 12430-12433.

DOI: 10.1021/jacs.7b07944 (free Supporting Information)


Abstract

In the presence of AgNO3 as the catalyst and K2S2O8 as the oxidant, reactions of aliphatic carboxylic acids with (bpy)Cu(CF3)3 and ZnMe2 in aqueous acetonitrile at 40C provide the corresponding decarboxylative trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl carboxylic acids and exhibits wide functional group compatibility.

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proposed mechanism



Trifluoromethylation of Alkyl Radicals in Aqueous Solution

H. Shen, Z. Liu, P. Zhang, X. Tan, Z. Zhang, C. Li, J. Am. Chem. Soc., 2017, 139, 9843-9846.


Key Words

trifluoromethyl alkanes, benzylic trifluoromethanes, potassium peroxydisulfate


ID: J48-Y2017