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.
Highlights
An air- and moisture-stable fluoroiodane in the presence of AgBF4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions
The early methods for introducing difluoromethyl groups to organic molecules were mainly based on the application of
Baran and co-workers have published a series of papers on CÀH difluoromethylation by CF2H radicals.[16]
Summary
An air- and moisture-stable fluoroiodane in the presence of AgBF4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions. Tang and co-workers[17] have shown that consecutive geminal difluorination of aromatic benzyl groups can be achieved by using Selectfluor as a fluorine source in combination with a silver catalyst under oxidative conditions.
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