Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

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.