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Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage

Electrochemical fluorinations of C(sp(3))−H bonds with a nucleophilic fluoride source have been accomplished in a chemo‐ and site‐selective fashion, avoiding the use of electrophilic F(+) sources and stoichiometric oxidants. The introduced metal‐free strategy exhibits high functional group tolerance...

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Detalles Bibliográficos
Autores principales: Stangier, Maximilian, Scheremetjew, Alexej, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804291/
https://www.ncbi.nlm.nih.gov/pubmed/35844078
http://dx.doi.org/10.1002/chem.202201654
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author Stangier, Maximilian
Scheremetjew, Alexej
Ackermann, Lutz
author_facet Stangier, Maximilian
Scheremetjew, Alexej
Ackermann, Lutz
author_sort Stangier, Maximilian
collection PubMed
description Electrochemical fluorinations of C(sp(3))−H bonds with a nucleophilic fluoride source have been accomplished in a chemo‐ and site‐selective fashion, avoiding the use of electrophilic F(+) sources and stoichiometric oxidants. The introduced metal‐free strategy exhibits high functional group tolerance, setting the stage for late‐stage fluorinations of biorelevant motifs. The synthetic utility of the C(sp(3))−H fluorination was reflected by subsequent one‐pot arylation of the generated benzylic fluorides.
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spelling pubmed-98042912023-01-03 Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage Stangier, Maximilian Scheremetjew, Alexej Ackermann, Lutz Chemistry Research Articles Electrochemical fluorinations of C(sp(3))−H bonds with a nucleophilic fluoride source have been accomplished in a chemo‐ and site‐selective fashion, avoiding the use of electrophilic F(+) sources and stoichiometric oxidants. The introduced metal‐free strategy exhibits high functional group tolerance, setting the stage for late‐stage fluorinations of biorelevant motifs. The synthetic utility of the C(sp(3))−H fluorination was reflected by subsequent one‐pot arylation of the generated benzylic fluorides. John Wiley and Sons Inc. 2022-08-31 2022-10-26 /pmc/articles/PMC9804291/ /pubmed/35844078 http://dx.doi.org/10.1002/chem.202201654 Text en © 2022 The Authors. Chemistry - A European Journal 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 Research Articles
Stangier, Maximilian
Scheremetjew, Alexej
Ackermann, Lutz
Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage
title Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage
title_full Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage
title_fullStr Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage
title_full_unstemmed Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage
title_short Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp(3))−H Cleavage
title_sort chemo‐ and site‐selective electro‐oxidative alkane fluorination by c(sp(3))−h cleavage
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804291/
https://www.ncbi.nlm.nih.gov/pubmed/35844078
http://dx.doi.org/10.1002/chem.202201654
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