Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.

ABSTRACT: An air- and moisture-stable fluoroiodane in the presence of AgBF4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions. One of the CF bonds is formed by transfer of electrophilic fluorine from the hypervalent iodine reagent, while the other one arises from the tetrafluoroborate counterion of silver. Deuterium-isotope-labelling experiments and rearrangement of methyl styrene substrates suggest that the reaction proceeds through a phenonium ion intermediate.

SUBMITTER: Ilchenko NO 

PROVIDER: S-EPMC4501311 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature