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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...

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Autores principales: Han, You-Feng, Huang, Ying, Liu, Hao, Gao, Zhong-Hua, Zhang, Chun-Lin, Ye, Song
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
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.
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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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