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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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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. |
format | Online Article Text |
id | pubmed-9828158 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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