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Benzylic C−H acylation by cooperative NHC and photoredox catalysis

Methods that enable site selective acylation of sp(3) C-H bonds in complex organic molecules are not well explored, particularly if compared with analogous transformations of aromatic and vinylic sp(2) C-H bonds. We report herein a direct acylation of benzylic C-H bonds by merging N-heterocyclic car...

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Autores principales: Meng, Qing-Yuan, Lezius, Lena, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8024347/
https://www.ncbi.nlm.nih.gov/pubmed/33824304
http://dx.doi.org/10.1038/s41467-021-22292-z
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author Meng, Qing-Yuan
Lezius, Lena
Studer, Armido
author_facet Meng, Qing-Yuan
Lezius, Lena
Studer, Armido
author_sort Meng, Qing-Yuan
collection PubMed
description Methods that enable site selective acylation of sp(3) C-H bonds in complex organic molecules are not well explored, particularly if compared with analogous transformations of aromatic and vinylic sp(2) C-H bonds. We report herein a direct acylation of benzylic C-H bonds by merging N-heterocyclic carbene (NHC) and photoredox catalysis. The method allows the preparation of a diverse range of benzylic ketones with good functional group tolerance under mild conditions. The reaction can be used to install acyl groups on highly functionalized natural product derived compounds and the C-H functionalization works with excellent site selectivity. The combination of NHC and photoredox catalysis offers options in preparing benzyl aryl ketones.
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spelling pubmed-80243472021-04-21 Benzylic C−H acylation by cooperative NHC and photoredox catalysis Meng, Qing-Yuan Lezius, Lena Studer, Armido Nat Commun Article Methods that enable site selective acylation of sp(3) C-H bonds in complex organic molecules are not well explored, particularly if compared with analogous transformations of aromatic and vinylic sp(2) C-H bonds. We report herein a direct acylation of benzylic C-H bonds by merging N-heterocyclic carbene (NHC) and photoredox catalysis. The method allows the preparation of a diverse range of benzylic ketones with good functional group tolerance under mild conditions. The reaction can be used to install acyl groups on highly functionalized natural product derived compounds and the C-H functionalization works with excellent site selectivity. The combination of NHC and photoredox catalysis offers options in preparing benzyl aryl ketones. Nature Publishing Group UK 2021-04-06 /pmc/articles/PMC8024347/ /pubmed/33824304 http://dx.doi.org/10.1038/s41467-021-22292-z Text en © The Author(s) 2021 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Meng, Qing-Yuan
Lezius, Lena
Studer, Armido
Benzylic C−H acylation by cooperative NHC and photoredox catalysis
title Benzylic C−H acylation by cooperative NHC and photoredox catalysis
title_full Benzylic C−H acylation by cooperative NHC and photoredox catalysis
title_fullStr Benzylic C−H acylation by cooperative NHC and photoredox catalysis
title_full_unstemmed Benzylic C−H acylation by cooperative NHC and photoredox catalysis
title_short Benzylic C−H acylation by cooperative NHC and photoredox catalysis
title_sort benzylic c−h acylation by cooperative nhc and photoredox catalysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8024347/
https://www.ncbi.nlm.nih.gov/pubmed/33824304
http://dx.doi.org/10.1038/s41467-021-22292-z
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