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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,...

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Detalles Bibliográficos
Autores principales: Zhong, Mingbing, Gagné, Yohann, Hope, Taylor O., Pannecoucke, Xavier, Frenette, Mathieu, Jubault, Philippe, Poisson, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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.
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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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