Electrochemical Umpolung C–H Functionalization of Oxindoles

[Image: see text] Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C–H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, e...

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Autores principales: Pastor, Miryam, Vayer, Marie, Weinstabl, Harald, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8749966/
https://www.ncbi.nlm.nih.gov/pubmed/34962127
http://dx.doi.org/10.1021/acs.joc.1c02616
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author Pastor, Miryam
Vayer, Marie
Weinstabl, Harald
Maulide, Nuno
author_facet Pastor, Miryam
Vayer, Marie
Weinstabl, Harald
Maulide, Nuno
author_sort Pastor, Miryam
collection PubMed
description [Image: see text] Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C–H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C–O, and by extension to C–C or even C–N bond formation.
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spelling pubmed-87499662022-01-11 Electrochemical Umpolung C–H Functionalization of Oxindoles Pastor, Miryam Vayer, Marie Weinstabl, Harald Maulide, Nuno J Org Chem [Image: see text] Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C–H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C–O, and by extension to C–C or even C–N bond formation. American Chemical Society 2021-12-28 2022-01-07 /pmc/articles/PMC8749966/ /pubmed/34962127 http://dx.doi.org/10.1021/acs.joc.1c02616 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Pastor, Miryam
Vayer, Marie
Weinstabl, Harald
Maulide, Nuno
Electrochemical Umpolung C–H Functionalization of Oxindoles
title Electrochemical Umpolung C–H Functionalization of Oxindoles
title_full Electrochemical Umpolung C–H Functionalization of Oxindoles
title_fullStr Electrochemical Umpolung C–H Functionalization of Oxindoles
title_full_unstemmed Electrochemical Umpolung C–H Functionalization of Oxindoles
title_short Electrochemical Umpolung C–H Functionalization of Oxindoles
title_sort electrochemical umpolung c–h functionalization of oxindoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8749966/
https://www.ncbi.nlm.nih.gov/pubmed/34962127
http://dx.doi.org/10.1021/acs.joc.1c02616
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AT vayermarie electrochemicalumpolungchfunctionalizationofoxindoles
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AT maulidenuno electrochemicalumpolungchfunctionalizationofoxindoles

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