Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
Pei Zhang, Haigen Shen, Xinqiang Tan, Chaozhong Li, Zhonglin Liu, Zhenzhen Zhang
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07944

DOI: 10.1021/jacs.7b07944

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