One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations

The strongly oxidizing, powerful electrophilic fluorination reagent [FXe][OTf] is shown to effect direct oxidative monofluorination of sulfoxides. This one‐step, chloride promoter‐free methodology provides access to so far inaccessible, yet highly desirable strongly Lewis acidic fluorosulfoxonium ca...

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Autores principales: Berreur, Jordan, Diez‐Varga, Alberto, Manel, Augustin, Leroux, Frédéric R., Panossian, Armen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10092253/
https://www.ncbi.nlm.nih.gov/pubmed/36047996
http://dx.doi.org/10.1002/chem.202202564
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author Berreur, Jordan
Diez‐Varga, Alberto
Manel, Augustin
Leroux, Frédéric R.
Panossian, Armen
author_facet Berreur, Jordan
Diez‐Varga, Alberto
Manel, Augustin
Leroux, Frédéric R.
Panossian, Armen
author_sort Berreur, Jordan
collection PubMed
description The strongly oxidizing, powerful electrophilic fluorination reagent [FXe][OTf] is shown to effect direct oxidative monofluorination of sulfoxides. This one‐step, chloride promoter‐free methodology provides access to so far inaccessible, yet highly desirable strongly Lewis acidic fluorosulfoxonium cations from electron‐deficient and/or sterically demanding sulfoxides that are shown to be practically unreactive towards the previously reported XeF(2)/NEt(4)Cl system. Experimental and density functional theory studies have been conducted to assess the Lewis acidities of the prepared sulfur(VI) cations. Preliminary results obtained with chiral sulfoxides provide early insights into the mechanism of these fluorination reactions.
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spelling pubmed-100922532023-04-13 One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations Berreur, Jordan Diez‐Varga, Alberto Manel, Augustin Leroux, Frédéric R. Panossian, Armen Chemistry Research Articles The strongly oxidizing, powerful electrophilic fluorination reagent [FXe][OTf] is shown to effect direct oxidative monofluorination of sulfoxides. This one‐step, chloride promoter‐free methodology provides access to so far inaccessible, yet highly desirable strongly Lewis acidic fluorosulfoxonium cations from electron‐deficient and/or sterically demanding sulfoxides that are shown to be practically unreactive towards the previously reported XeF(2)/NEt(4)Cl system. Experimental and density functional theory studies have been conducted to assess the Lewis acidities of the prepared sulfur(VI) cations. Preliminary results obtained with chiral sulfoxides provide early insights into the mechanism of these fluorination reactions. John Wiley and Sons Inc. 2022-10-19 2022-12-09 /pmc/articles/PMC10092253/ /pubmed/36047996 http://dx.doi.org/10.1002/chem.202202564 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Berreur, Jordan
Diez‐Varga, Alberto
Manel, Augustin
Leroux, Frédéric R.
Panossian, Armen
One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
title One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
title_full One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
title_fullStr One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
title_full_unstemmed One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
title_short One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
title_sort one‐step oxidative monofluorination of electron‐deficient sulfoxides to access highly lewis acidic sulfur(vi) cations
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10092253/
https://www.ncbi.nlm.nih.gov/pubmed/36047996
http://dx.doi.org/10.1002/chem.202202564
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