Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates

The electrophilic fluorination of geminal alkyl substituted vinyl‐Bmida derivatives proceeds via bora‐Wagner–Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora‐cyclopropane shaped TS. The Bmida group has a larger migration ap...

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Detalles Bibliográficos
Autores principales: Wang, Qiang, Biosca, Maria, Himo, Fahmi, Szabó, Kálmán J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9299629/
https://www.ncbi.nlm.nih.gov/pubmed/34613633
http://dx.doi.org/10.1002/anie.202109461
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author Wang, Qiang
Biosca, Maria
Himo, Fahmi
Szabó, Kálmán J.
author_facet Wang, Qiang
Biosca, Maria
Himo, Fahmi
Szabó, Kálmán J.
author_sort Wang, Qiang
collection PubMed
description The electrophilic fluorination of geminal alkyl substituted vinyl‐Bmida derivatives proceeds via bora‐Wagner–Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora‐cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner–Meerwein rearrangement of the presented electrophilic fluorination reactions.
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spelling pubmed-92996292022-07-21 Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates Wang, Qiang Biosca, Maria Himo, Fahmi Szabó, Kálmán J. Angew Chem Int Ed Engl Communications The electrophilic fluorination of geminal alkyl substituted vinyl‐Bmida derivatives proceeds via bora‐Wagner–Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora‐cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner–Meerwein rearrangement of the presented electrophilic fluorination reactions. John Wiley and Sons Inc. 2021-11-10 2021-12-06 /pmc/articles/PMC9299629/ /pubmed/34613633 http://dx.doi.org/10.1002/anie.202109461 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Wang, Qiang
Biosca, Maria
Himo, Fahmi
Szabó, Kálmán J.
Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates
title Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates
title_full Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates
title_fullStr Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates
title_full_unstemmed Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates
title_short Electrophilic Fluorination of Alkenes via Bora‐Wagner–Meerwein Rearrangement. Access to β‐Difluoroalkyl Boronates
title_sort electrophilic fluorination of alkenes via bora‐wagner–meerwein rearrangement. access to β‐difluoroalkyl boronates
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9299629/
https://www.ncbi.nlm.nih.gov/pubmed/34613633
http://dx.doi.org/10.1002/anie.202109461
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