title: 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.
authors.affiliation: Department of Organic Chemistry, Stockholm University http://www.organ.su.se/ks/
authors.forename: Nadia O
authors.initials: NO
authors.lastname: Ilchenko
authors.forename: Boris O A
authors.initials: BO
authors.lastname: Tasch
authors.forename: Kálmán J
authors.initials: KJ
authors.lastname: Szabó
mesh_terms: D000388:Air; D001881:Borates / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry; D054879:Halogenation; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D001881:Borates; D006574:Heterocyclic Compounds, 2-Ring; D006845:Hydrocarbons, Fluorinated; D009861:Onium Compounds; D018030:Silver Compounds; D013343:Styrenes; D014867:Water; C064097:silver tetrafluoroborate; D003903:Deuterium
keywords: fluorine; hypervalent compounds; reaction mechanism; rearrangement; silver