Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism

Abstract

H/D Isotope effects in fluorination of aromatic compounds with NF type reagents have been studied to reveal the reaction mechanism. The results obtained are consistent with a polar S EAr mechanism. Small deuterium isotope effects ( k H/ k D = 0.86–0.99) show that decomposition of a Wheland-type intermediate is not rate determining. The first example of a 1,2-hydrogen shift accompanying electrophilic fluorination of arenes has been observed in the fluorination of 1,3,5-trideuterobenzene.