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Organocatalyzed Fluoride Metathesis
preprintsubmitted on 01.09.2020, 09:22 and posted on 01.09.2020, 13:05 by Mark Crimmin, Daniel Mulryan, Andrew J. P. White
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.