Copper-Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me4N][SeCF3]

Abstract

The synthesis of alkynyl trifluoromethyl selenoethers from copper-mediated aerobic decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with [Me₄N][SeCF₃] is reported. The reaction proceeded smoothly under mild conditions and enabled the facile conversion of both aryl and alkyl alkynyl carboxylic acids to the corresponding trifluoromethyl selenoethers in good yields, demonstrating that decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with the nucleophilic [Me₄N][SeCF₃] reagent is feasible at ambient temperature without irradiation. Advantages of the method include the use of bench-stable and non-volatile alkynyl carboxylic acids as starting materials, readily accessible SeCF₃ reagent, excellent functional group tolerance, and the avoidance of harsh reaction conditions. This copper-mediated reaction represents the first decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with a SeCF₃ source.