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Updated: Feb 24, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
Xinqiang Tan1, Zhonglin Liu1, Haigen Shen1
1Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Abstract:
The silver-catalyzed decarboxylative trifluoromethylation of aliphatic carboxylic acids is described. With AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of aliphatic carboxylic acids with (bpy)Cu(CF3)3 (bpy = 2,2'-bipyridine) and ZnMe2 in aqueous acetonitrile at 40 °C afford 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. Mechanistic studies reveal the intermediacy of -Cu(CF3)3Me, which undergoes reductive elimination and subsequent oxidation to give Cu(CF3)2 as the active species responsible for the trifluoromethylation of alkyl radicals.
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