Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**

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 C=F bonds is formed by transfer of electrophilic fluorine from the hypervalent iodine reagent, while the other one arises from t...

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Detalles Bibliográficos
Autores principales: Ilchenko, Nadia O, Tasch, Boris O A, Szabó, Kálmán J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4501311/
https://www.ncbi.nlm.nih.gov/pubmed/25335468
http://dx.doi.org/10.1002/anie.201408812
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author Ilchenko, Nadia O
Tasch, Boris O A
Szabó, Kálmán J
author_facet Ilchenko, Nadia O
Tasch, Boris O A
Szabó, Kálmán J
author_sort Ilchenko, Nadia O
collection PubMed
description 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 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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spelling pubmed-45013112015-07-21 Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent** Ilchenko, Nadia O Tasch, Boris O A Szabó, Kálmán J Angew Chem Int Ed Engl Communications 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 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. WILEY-VCH Verlag 2014-11-17 2014-10-21 /pmc/articles/PMC4501311/ /pubmed/25335468 http://dx.doi.org/10.1002/anie.201408812 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by/3.0/ This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited
spellingShingle Communications
Ilchenko, Nadia O
Tasch, Boris O A
Szabó, Kálmán J
Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**
title Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**
title_full Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**
title_fullStr Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**
title_full_unstemmed Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**
title_short Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent**
title_sort mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4501311/
https://www.ncbi.nlm.nih.gov/pubmed/25335468
http://dx.doi.org/10.1002/anie.201408812
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