Selective C4-F bond cleavage of pentafluorobenzene: synthesis of N-tetrafluoroarylated heterocyclic compounds

A simple aromatic nucleophilic monosubstitution reaction for the synthesis of N-tetrafluoroarylated heterocyclic compounds via selective C4-F bond cleavage of pentafluorobenzene with N-H containing heterocycles is demonstrated. This method is highly tolerant of a wide range of substrates to give the corresponding products in moderate to good yields. Additionally, this strategy is applied to synthesize other mono-, di-, and tri-fluoroarylated indole derivatives.