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...

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Autores principales: Delfau, Ludivine, Assani, Nadhrata, Nichilo, Samantha, Pecaut, Jacques, Philouze, Christian, Broggi, Julie, Martin, David, Tomás-Mendivil, Eder
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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