Organocatalyzed Fluoride Metathesis

A new organocatalyzed fluoride metathesis reaction between fluoroarenes and carbonyl derivatives is reported. The reaction exchanges fluoride (F–) and alternate nucleophiles (OAc–, CO2R–, SR–, Cl–, CN–, NCS–). The approach provides a conceptually novel route to manipulate the fluorine content of organic molecules. By combining fluorination and defluorination steps into a single catalytic cycle, a byproduct free and 100% atom-efficient reaction can be achieved.