Mild Silver‐Mediated Geminal Difluorination of Styrenes Using an Air‐ and Moisture‐Stable Fluoroiodane Reagent |
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| Authors: | Nadia O. Ilchenko Dr. Boris O. A. Tasch Prof. Kálmán J. Szabó |
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| Affiliation: | Department of Organic Chemistry, Stockholm University http://www.organ.su.se/ks/ |
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| 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. |
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| Keywords: | fluorine hypervalent compounds reaction mechanism rearrangement silver |
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