Organic Photoredox-Catalyzed Decarboxylative Trifluoromethylselenolation of Aliphatic Carboxylic Acids with [Me₄N][SeCF₃]

Abstract

Oxidative decarboxylation/trifluoromethylselenolation of primary, secondary, and tertiary aliphatic carboxylic acids with the nucleophilic [Me₄N][SeCF₃] salt and an organic photocatalyst is described. The reaction proceeds smoothly at room temperature under transition-metal-free conditions and affords the corresponding trifluoromethylselenolated products in good yields. Advantages of the method include good functional group tolerance, without preactivation of the acids, and late-stage functionalization of the complex drug molecules. This protocol represents the first decarboxylative trifluoromethylselenolation of carboxylic acids to trifluoromethyl selenoethers.