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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


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 40°C 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


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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