Organocatalyzed Fluoride Metathesis

Organic Letters
Daniel MulryanMark Crimmin

Abstract

A new organocatalyzed fluoride metathesis reaction between fluoroarenes and carbonyl derivatives is reported. The reaction exchanges fluoride (F-) and alternate nucleophiles (OAc-, OCO2R-, SR-, Cl-, CN-, NCS-). The approach provides a conceptually novel route to manipulate the fluorine content of organic molecules. When the fluorination and defluorination steps are combined into a single catalytic cycle, a byproduct free and 100% atom-efficient reaction can be achieved.

References

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