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Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

Four-component coupling reactions between xanthogenates, alkenes, CO, and sulfonyl oxime ethers were studied. In the presence of hexabutylditin, working as a propagating radical reagent, the chain reaction proceeds, as expected, taking into account reagents polarities, affording the corresponding fu...

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Autores principales: Sumino, Shuhei, Fukuyama, Takahide, Sasano, Mika, Ryu, Ilhyong, Jacquet, Antoine, Robert, Frédéric, Landais, Yannick
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6693370/
https://www.ncbi.nlm.nih.gov/pubmed/31467602
http://dx.doi.org/10.3762/bjoc.15.176
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author Sumino, Shuhei
Fukuyama, Takahide
Sasano, Mika
Ryu, Ilhyong
Jacquet, Antoine
Robert, Frédéric
Landais, Yannick
author_facet Sumino, Shuhei
Fukuyama, Takahide
Sasano, Mika
Ryu, Ilhyong
Jacquet, Antoine
Robert, Frédéric
Landais, Yannick
author_sort Sumino, Shuhei
collection PubMed
description Four-component coupling reactions between xanthogenates, alkenes, CO, and sulfonyl oxime ethers were studied. In the presence of hexabutylditin, working as a propagating radical reagent, the chain reaction proceeds, as expected, taking into account reagents polarities, affording the corresponding functionalized α-keto oximes. Although yields are modest, this rare one-pot four-component process is easy to carry out and the resulting compounds, bearing multiple functionalities, have the potential for further elaboration.
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spelling pubmed-66933702019-08-29 Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers Sumino, Shuhei Fukuyama, Takahide Sasano, Mika Ryu, Ilhyong Jacquet, Antoine Robert, Frédéric Landais, Yannick Beilstein J Org Chem Letter Four-component coupling reactions between xanthogenates, alkenes, CO, and sulfonyl oxime ethers were studied. In the presence of hexabutylditin, working as a propagating radical reagent, the chain reaction proceeds, as expected, taking into account reagents polarities, affording the corresponding functionalized α-keto oximes. Although yields are modest, this rare one-pot four-component process is easy to carry out and the resulting compounds, bearing multiple functionalities, have the potential for further elaboration. Beilstein-Institut 2019-07-31 /pmc/articles/PMC6693370/ /pubmed/31467602 http://dx.doi.org/10.3762/bjoc.15.176 Text en Copyright © 2019, Sumino et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Sumino, Shuhei
Fukuyama, Takahide
Sasano, Mika
Ryu, Ilhyong
Jacquet, Antoine
Robert, Frédéric
Landais, Yannick
Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers
title Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers
title_full Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers
title_fullStr Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers
title_full_unstemmed Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers
title_short Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers
title_sort vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, co, and sulfonyl oxime ethers
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6693370/
https://www.ncbi.nlm.nih.gov/pubmed/31467602
http://dx.doi.org/10.3762/bjoc.15.176
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