Organocatalyzed Fluoride Metathesis

Org Lett. 2020 Dec 4;22(23):9351-9355. doi: 10.1021/acs.orglett.0c03593. Epub 2020 Nov 17.

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.