Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocat...

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Autores principales: Supranovich, Vyacheslav I, Dmitriev, Igor A, Dilman, Alexander D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783028/
https://www.ncbi.nlm.nih.gov/pubmed/33437323
http://dx.doi.org/10.3762/bjoc.16.260
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author Supranovich, Vyacheslav I
Dmitriev, Igor A
Dilman, Alexander D
author_facet Supranovich, Vyacheslav I
Dmitriev, Igor A
Dilman, Alexander D
author_sort Supranovich, Vyacheslav I
collection PubMed
description A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N–O bond.
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spelling pubmed-77830282021-01-11 Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction Supranovich, Vyacheslav I Dmitriev, Igor A Dilman, Alexander D Beilstein J Org Chem Letter A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N–O bond. Beilstein-Institut 2020-12-29 /pmc/articles/PMC7783028/ /pubmed/33437323 http://dx.doi.org/10.3762/bjoc.16.260 Text en Copyright © 2020, Supranovich et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/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 author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Letter
Supranovich, Vyacheslav I
Dmitriev, Igor A
Dilman, Alexander D
Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_full Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_fullStr Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_full_unstemmed Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_short Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_sort synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783028/
https://www.ncbi.nlm.nih.gov/pubmed/33437323
http://dx.doi.org/10.3762/bjoc.16.260
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