Palladium-Assisted Room-Temperature Nucleophilic Substitution of an Unactivated Aryl Fluoride

An organometallic palladium(II) complex of an 8-fluoroquinoline-based chelating ligand undergoes very facile nucleophilic substitution of the unactivated fluorine atom with the methoxy group upon simple stirring of its THF solution with sodium methoxide at room temperature. The final product of this reaction lacks the aromaticity in the heterocyclic ring of the quinoline moiety which might play an important role in the overall reactivity.