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Direct sulfonylation of anilines mediated by visible light

Sulfones feature prominently in biologically active molecules and are key functional groups for organic synthesis. We report a mild, photoredox-catalyzed reaction for sulfonylation of aniline derivatives with sulfinate salts, and demonstrate the utility of the method by the late-stage functionalizat...

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Autores principales: Johnson, Tarn C., Elbert, Bryony L., Farley, Alistair J. M., Gorman, Timothy W., Genicot, Christophe, Lallemand, Bénédicte, Pasau, Patrick, Flasz, Jakub, Castro, José L., MacCoss, Malcolm, Dixon, Darren J., Paton, Robert S., Schofield, Christopher J., Smith, Martin D., Willis, Michael C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5868301/
https://www.ncbi.nlm.nih.gov/pubmed/29629128
http://dx.doi.org/10.1039/c7sc03891g
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author Johnson, Tarn C.
Elbert, Bryony L.
Farley, Alistair J. M.
Gorman, Timothy W.
Genicot, Christophe
Lallemand, Bénédicte
Pasau, Patrick
Flasz, Jakub
Castro, José L.
MacCoss, Malcolm
Dixon, Darren J.
Paton, Robert S.
Schofield, Christopher J.
Smith, Martin D.
Willis, Michael C.
author_facet Johnson, Tarn C.
Elbert, Bryony L.
Farley, Alistair J. M.
Gorman, Timothy W.
Genicot, Christophe
Lallemand, Bénédicte
Pasau, Patrick
Flasz, Jakub
Castro, José L.
MacCoss, Malcolm
Dixon, Darren J.
Paton, Robert S.
Schofield, Christopher J.
Smith, Martin D.
Willis, Michael C.
author_sort Johnson, Tarn C.
collection PubMed
description Sulfones feature prominently in biologically active molecules and are key functional groups for organic synthesis. We report a mild, photoredox-catalyzed reaction for sulfonylation of aniline derivatives with sulfinate salts, and demonstrate the utility of the method by the late-stage functionalization of drugs. Key features of the method are the straightforward generation of sulfonyl radicals from bench-stable sulfinate salts and the use of simple aniline derivatives as convenient readily available coupling partners.
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spelling pubmed-58683012018-04-06 Direct sulfonylation of anilines mediated by visible light Johnson, Tarn C. Elbert, Bryony L. Farley, Alistair J. M. Gorman, Timothy W. Genicot, Christophe Lallemand, Bénédicte Pasau, Patrick Flasz, Jakub Castro, José L. MacCoss, Malcolm Dixon, Darren J. Paton, Robert S. Schofield, Christopher J. Smith, Martin D. Willis, Michael C. Chem Sci Chemistry Sulfones feature prominently in biologically active molecules and are key functional groups for organic synthesis. We report a mild, photoredox-catalyzed reaction for sulfonylation of aniline derivatives with sulfinate salts, and demonstrate the utility of the method by the late-stage functionalization of drugs. Key features of the method are the straightforward generation of sulfonyl radicals from bench-stable sulfinate salts and the use of simple aniline derivatives as convenient readily available coupling partners. Royal Society of Chemistry 2017-11-16 /pmc/articles/PMC5868301/ /pubmed/29629128 http://dx.doi.org/10.1039/c7sc03891g Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Johnson, Tarn C.
Elbert, Bryony L.
Farley, Alistair J. M.
Gorman, Timothy W.
Genicot, Christophe
Lallemand, Bénédicte
Pasau, Patrick
Flasz, Jakub
Castro, José L.
MacCoss, Malcolm
Dixon, Darren J.
Paton, Robert S.
Schofield, Christopher J.
Smith, Martin D.
Willis, Michael C.
Direct sulfonylation of anilines mediated by visible light
title Direct sulfonylation of anilines mediated by visible light
title_full Direct sulfonylation of anilines mediated by visible light
title_fullStr Direct sulfonylation of anilines mediated by visible light
title_full_unstemmed Direct sulfonylation of anilines mediated by visible light
title_short Direct sulfonylation of anilines mediated by visible light
title_sort direct sulfonylation of anilines mediated by visible light
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5868301/
https://www.ncbi.nlm.nih.gov/pubmed/29629128
http://dx.doi.org/10.1039/c7sc03891g
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