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On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis
[Image: see text] We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (E(ox) = −0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied i...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10251502/ https://www.ncbi.nlm.nih.gov/pubmed/37303499 http://dx.doi.org/10.1021/acsorginorgau.3c00008 |
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author | Delfau, Ludivine Assani, Nadhrata Nichilo, Samantha Pecaut, Jacques Philouze, Christian Broggi, Julie Martin, David Tomás-Mendivil, Eder |
author_facet | Delfau, Ludivine Assani, Nadhrata Nichilo, Samantha Pecaut, Jacques Philouze, Christian Broggi, Julie Martin, David Tomás-Mendivil, Eder |
author_sort | Delfau, Ludivine |
collection | PubMed |
description | [Image: see text] We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (E(ox) = −0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in the literature. In addition, a remarkable potential gap between the first and second oxidation of the dimer also allows for the isolation of the corresponding air-persistent radical cation. The latter is an unexpected efficient promoter of the radical transformation of α-bromoamides into oxindoles. |
format | Online Article Text |
id | pubmed-10251502 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-102515022023-06-10 On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis Delfau, Ludivine Assani, Nadhrata Nichilo, Samantha Pecaut, Jacques Philouze, Christian Broggi, Julie Martin, David Tomás-Mendivil, Eder ACS Org Inorg Au [Image: see text] We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (E(ox) = −0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in the literature. In addition, a remarkable potential gap between the first and second oxidation of the dimer also allows for the isolation of the corresponding air-persistent radical cation. The latter is an unexpected efficient promoter of the radical transformation of α-bromoamides into oxindoles. American Chemical Society 2023-03-27 /pmc/articles/PMC10251502/ /pubmed/37303499 http://dx.doi.org/10.1021/acsorginorgau.3c00008 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Delfau, Ludivine Assani, Nadhrata Nichilo, Samantha Pecaut, Jacques Philouze, Christian Broggi, Julie Martin, David Tomás-Mendivil, Eder On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis |
title | On the Redox
Properties of the Dimers of Thiazol-2-ylidenes
That Are Relevant for Radical Catalysis |
title_full | On the Redox
Properties of the Dimers of Thiazol-2-ylidenes
That Are Relevant for Radical Catalysis |
title_fullStr | On the Redox
Properties of the Dimers of Thiazol-2-ylidenes
That Are Relevant for Radical Catalysis |
title_full_unstemmed | On the Redox
Properties of the Dimers of Thiazol-2-ylidenes
That Are Relevant for Radical Catalysis |
title_short | On the Redox
Properties of the Dimers of Thiazol-2-ylidenes
That Are Relevant for Radical Catalysis |
title_sort | on the redox
properties of the dimers of thiazol-2-ylidenes
that are relevant for radical catalysis |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10251502/ https://www.ncbi.nlm.nih.gov/pubmed/37303499 http://dx.doi.org/10.1021/acsorginorgau.3c00008 |
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