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

Authors :: Ilchenko NO
Tasch BO
Szabó KJ
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2014 Nov 17; Vol. 53 (47), pp. 12897-901. Date of Electronic Publication: 2014 Oct 21.
Publication Year :: 2014
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.<br /> (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Air
Deuterium chemistry
Halogenation
Hydrocarbons, Fluorinated chemistry
Molecular Structure
Water chemistry
Borates chemistry
Heterocyclic Compounds, 2-Ring chemistry
Hydrocarbons, Fluorinated chemical synthesis
Onium Compounds chemistry
Silver Compounds chemistry
Styrenes chemistry

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