C–F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene

Abstract

The N-heterocyclic carbene IBioxMe₄ enacts selective single and double C-F bond activation of octafluorotoluene and hexafluorobenzene, respectively. The formation of the fluoroarene substituted, zwitterionic imidazoliumolate products is consistent with a mechanism involving nucleophilic aromatic substitution and subsequent oxazoline ring opening by liberated fluoride.