Electro-oxidative Deoxyfluorination of Arenes with NEt3·3HF

This report describes the design, development, and optimization of an electrochemical deoxyfluorination of arenes using a tetrafluoropyridine-derived leaving group. NEt3·3HF serves as the fluoride source, and the reactions are conducted using either constant potential or constant current electrolysis in an undivided electrochemical cell. Mechanistic studies support a net oxidative pathway, in which initial single-electron oxidation generates a radical cation intermediate that is trapped by fluoride. The resulting radical undergoes a second oxidation reaction, followed by the loss of the leaving group to yield the fluoroarene product.