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Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes
Three-component carboacylation of simple alkenes with readily available reagents is challenging. Transition metal-catalysed intermolecular carboacylation works for alkenes with strained ring or directing groups. Herein, we develop a photoredox cooperative N-heterocyclic carbene/Pd-catalysed alkylacy...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9525644/ https://www.ncbi.nlm.nih.gov/pubmed/36180483 http://dx.doi.org/10.1038/s41467-022-33444-0 |
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author | Han, You-Feng Huang, Ying Liu, Hao Gao, Zhong-Hua Zhang, Chun-Lin Ye, Song |
author_facet | Han, You-Feng Huang, Ying Liu, Hao Gao, Zhong-Hua Zhang, Chun-Lin Ye, Song |
author_sort | Han, You-Feng |
collection | PubMed |
description | Three-component carboacylation of simple alkenes with readily available reagents is challenging. Transition metal-catalysed intermolecular carboacylation works for alkenes with strained ring or directing groups. Herein, we develop a photoredox cooperative N-heterocyclic carbene/Pd-catalysed alkylacylation of simple alkenes with aldehydes and unactivated alkyl halides to provide ketones in good yields. This multicomponent coupling reaction features a wide scope of alkenes, broad functional group compatibility and free of exogenous photosensitizer or external reductant. In addition, a series of chlorinated cyclopropanes with one or two vicinal quaternary carbons is obtained when chloroform or carbon tetrachloride is used as the alkyl halide. The reaction involves the alkyl radicals from halides and the ketyl radicals from aldehydes under photoredox cooperative N-heterocyclic carbene/Pd catalysis. |
format | Online Article Text |
id | pubmed-9525644 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-95256442022-10-02 Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes Han, You-Feng Huang, Ying Liu, Hao Gao, Zhong-Hua Zhang, Chun-Lin Ye, Song Nat Commun Article Three-component carboacylation of simple alkenes with readily available reagents is challenging. Transition metal-catalysed intermolecular carboacylation works for alkenes with strained ring or directing groups. Herein, we develop a photoredox cooperative N-heterocyclic carbene/Pd-catalysed alkylacylation of simple alkenes with aldehydes and unactivated alkyl halides to provide ketones in good yields. This multicomponent coupling reaction features a wide scope of alkenes, broad functional group compatibility and free of exogenous photosensitizer or external reductant. In addition, a series of chlorinated cyclopropanes with one or two vicinal quaternary carbons is obtained when chloroform or carbon tetrachloride is used as the alkyl halide. The reaction involves the alkyl radicals from halides and the ketyl radicals from aldehydes under photoredox cooperative N-heterocyclic carbene/Pd catalysis. Nature Publishing Group UK 2022-09-30 /pmc/articles/PMC9525644/ /pubmed/36180483 http://dx.doi.org/10.1038/s41467-022-33444-0 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/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/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Han, You-Feng Huang, Ying Liu, Hao Gao, Zhong-Hua Zhang, Chun-Lin Ye, Song Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
title | Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
title_full | Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
title_fullStr | Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
title_full_unstemmed | Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
title_short | Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
title_sort | photoredox cooperative n-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9525644/ https://www.ncbi.nlm.nih.gov/pubmed/36180483 http://dx.doi.org/10.1038/s41467-022-33444-0 |
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