Harnessing the Radical Reactivity of Silver(II) Fluoride for Organofluorine Synthesis

Most practical fluorination reagents deliver a fluorine atom either as a nucleophile (F–) or as an electrophile (F+). In contrast, bench-stable radical fluorine (F•) reagents are relatively less common and the vast majority of ‘radical fluorinations’ involve reactions of carbon-centered radicals with electrophilic fluorination reagents. Here, we disclose that silver (II) fluoride (AgF2) in acetonitrile is a mild source of F• that can be leveraged for the synthesis of a variety of high-value organofluorine compounds from abundantly available reactants such as alkanes, alkenes, and carboxylic acids, as well as from pharmaceutically relevant heterocycles such as indoles and benzofurans. This platform technology obviates the need for expensive catalysts and fluorinating reagents that are typically necessary to accomplish these transformations and relies on the use of AgF2 in acetonitrile as the sole reagent under mild conditions.