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Mild Silver‐Mediated Geminal Difluorination of Styrenes Using an Air‐ and Moisture‐Stable Fluoroiodane Reagent
Author(s) -
Ilchenko Nadia O.,
Tasch Boris O. A.,
Szabó Kálmán J.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408812
Subject(s) - geminal , chemistry , reagent , hypervalent molecule , electrophile , counterion , deuterium , tetrafluoroborate , moisture , styrene , organic chemistry , photochemistry , ion , catalysis , physics , ionic liquid , polymer , quantum mechanics , copolymer
An air‐ and moisture‐stable fluoroiodane in the presence of AgBF 4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions. One of the CF 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.