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Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes
The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly‐designed copper photocatalysts with B(2)Pin(2) permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields,...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252632/ https://www.ncbi.nlm.nih.gov/pubmed/33780588 http://dx.doi.org/10.1002/anie.202101874 |
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author | Zhong, Mingbing Gagné, Yohann Hope, Taylor O. Pannecoucke, Xavier Frenette, Mathieu Jubault, Philippe Poisson, Thomas |
author_facet | Zhong, Mingbing Gagné, Yohann Hope, Taylor O. Pannecoucke, Xavier Frenette, Mathieu Jubault, Philippe Poisson, Thomas |
author_sort | Zhong, Mingbing |
collection | PubMed |
description | The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly‐designed copper photocatalysts with B(2)Pin(2) permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu‐photocatalyst in its excited state for the boryl radical formation. |
format | Online Article Text |
id | pubmed-8252632 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-82526322021-07-09 Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes Zhong, Mingbing Gagné, Yohann Hope, Taylor O. Pannecoucke, Xavier Frenette, Mathieu Jubault, Philippe Poisson, Thomas Angew Chem Int Ed Engl Research Articles The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly‐designed copper photocatalysts with B(2)Pin(2) permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu‐photocatalyst in its excited state for the boryl radical formation. John Wiley and Sons Inc. 2021-05-17 2021-06-21 /pmc/articles/PMC8252632/ /pubmed/33780588 http://dx.doi.org/10.1002/anie.202101874 Text en © 2021 The Authors. Angewandte Chemie International Edition 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 Zhong, Mingbing Gagné, Yohann Hope, Taylor O. Pannecoucke, Xavier Frenette, Mathieu Jubault, Philippe Poisson, Thomas Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes |
title | Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes |
title_full | Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes |
title_fullStr | Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes |
title_full_unstemmed | Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes |
title_short | Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes |
title_sort | copper‐photocatalyzed hydroboration of alkynes and alkenes |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252632/ https://www.ncbi.nlm.nih.gov/pubmed/33780588 http://dx.doi.org/10.1002/anie.202101874 |
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