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Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay

The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component m...

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Autores principales: Zhao, Xian, Tu, Hai-Yong, Guo, Lei, Zhu, Shengqing, Qing, Feng-Ling, Chu, Lingling
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6113317/
https://www.ncbi.nlm.nih.gov/pubmed/30154495
http://dx.doi.org/10.1038/s41467-018-05951-6
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author Zhao, Xian
Tu, Hai-Yong
Guo, Lei
Zhu, Shengqing
Qing, Feng-Ling
Chu, Lingling
author_facet Zhao, Xian
Tu, Hai-Yong
Guo, Lei
Zhu, Shengqing
Qing, Feng-Ling
Chu, Lingling
author_sort Zhao, Xian
collection PubMed
description The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel complex to forge two vicinal C−C bonds under mild conditions. Excellent chemoselectivity and regioselectivity have been achieved by utilizing a pendant weakly chelating group. This versatile protocol allows for facile access to a wide range of important β-fluoroalkyl ketones from simple starting materials.
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spelling pubmed-61133172018-08-30 Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay Zhao, Xian Tu, Hai-Yong Guo, Lei Zhu, Shengqing Qing, Feng-Ling Chu, Lingling Nat Commun Article The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel complex to forge two vicinal C−C bonds under mild conditions. Excellent chemoselectivity and regioselectivity have been achieved by utilizing a pendant weakly chelating group. This versatile protocol allows for facile access to a wide range of important β-fluoroalkyl ketones from simple starting materials. Nature Publishing Group UK 2018-08-28 /pmc/articles/PMC6113317/ /pubmed/30154495 http://dx.doi.org/10.1038/s41467-018-05951-6 Text en © The Author(s) 2018 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
Zhao, Xian
Tu, Hai-Yong
Guo, Lei
Zhu, Shengqing
Qing, Feng-Ling
Chu, Lingling
Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
title Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
title_full Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
title_fullStr Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
title_full_unstemmed Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
title_short Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
title_sort intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6113317/
https://www.ncbi.nlm.nih.gov/pubmed/30154495
http://dx.doi.org/10.1038/s41467-018-05951-6
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