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Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes

The electrochemical synthesis of fluorinated allyl silanes and boronates was disclosed. The addition of electrogenerated boryl or silyl radicals onto many α‐trifluoromethyl or α‐difluoromethylstyrenes in an undivided cell allowed the formation of a large panel of synthetically useful gem‐difluoro an...

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Autores principales: Aelterman, Maude, Biremond, Tony, Jubault, Philippe, Poisson, Thomas
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/PMC9828158/
https://www.ncbi.nlm.nih.gov/pubmed/36067044
http://dx.doi.org/10.1002/chem.202202194
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author Aelterman, Maude
Biremond, Tony
Jubault, Philippe
Poisson, Thomas
author_facet Aelterman, Maude
Biremond, Tony
Jubault, Philippe
Poisson, Thomas
author_sort Aelterman, Maude
collection PubMed
description The electrochemical synthesis of fluorinated allyl silanes and boronates was disclosed. The addition of electrogenerated boryl or silyl radicals onto many α‐trifluoromethyl or α‐difluoromethylstyrenes in an undivided cell allowed the formation of a large panel of synthetically useful gem‐difluoro and γ‐fluoroallyl boronates and silanes (64 examples, from 31 % to 95 % yield). In addition, a scale up of the reactions under continuous flow was showcased using an electrochemical reactor with promising volumetric productivity (688 g.L(−1).h(−1) and 496 g.L(−1).h(−1)). Moreover, the synthetic utility of these building blocks was highlighted through versatile transformations. Finally, plausible reaction mechanisms were suggested to explain the formation of the products.
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spelling pubmed-98281582023-01-10 Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes Aelterman, Maude Biremond, Tony Jubault, Philippe Poisson, Thomas Chemistry Research Articles The electrochemical synthesis of fluorinated allyl silanes and boronates was disclosed. The addition of electrogenerated boryl or silyl radicals onto many α‐trifluoromethyl or α‐difluoromethylstyrenes in an undivided cell allowed the formation of a large panel of synthetically useful gem‐difluoro and γ‐fluoroallyl boronates and silanes (64 examples, from 31 % to 95 % yield). In addition, a scale up of the reactions under continuous flow was showcased using an electrochemical reactor with promising volumetric productivity (688 g.L(−1).h(−1) and 496 g.L(−1).h(−1)). Moreover, the synthetic utility of these building blocks was highlighted through versatile transformations. Finally, plausible reaction mechanisms were suggested to explain the formation of the products. John Wiley and Sons Inc. 2022-09-26 2022-11-25 /pmc/articles/PMC9828158/ /pubmed/36067044 http://dx.doi.org/10.1002/chem.202202194 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
Aelterman, Maude
Biremond, Tony
Jubault, Philippe
Poisson, Thomas
Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes
title Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes
title_full Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes
title_fullStr Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes
title_full_unstemmed Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes
title_short Electrochemical Synthesis of gem‐Difluoro‐ and γ‐Fluoro‐Allyl Boronates and Silanes
title_sort electrochemical synthesis of gem‐difluoro‐ and γ‐fluoro‐allyl boronates and silanes
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828158/
https://www.ncbi.nlm.nih.gov/pubmed/36067044
http://dx.doi.org/10.1002/chem.202202194
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