Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines

[Image: see text] There is an urgent need to develop uncharged radical precursors to be activated under mild photocatalyzed conditions. 2-Substituted-1,3-oxazolidines (E(ox) < 1.3 V vs SCE, smoothly prepared from the corresponding aldehydes) have been herein employed for the successful release of...

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Autores principales: Luguera Ruiz, Adrián, La Mantia, Marta, Merli, Daniele, Protti, Stefano, Fagnoni, Maurizio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552967/
https://www.ncbi.nlm.nih.gov/pubmed/36249874
http://dx.doi.org/10.1021/acscatal.2c03768
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author Luguera Ruiz, Adrián
La Mantia, Marta
Merli, Daniele
Protti, Stefano
Fagnoni, Maurizio
author_facet Luguera Ruiz, Adrián
La Mantia, Marta
Merli, Daniele
Protti, Stefano
Fagnoni, Maurizio
author_sort Luguera Ruiz, Adrián
collection PubMed
description [Image: see text] There is an urgent need to develop uncharged radical precursors to be activated under mild photocatalyzed conditions. 2-Substituted-1,3-oxazolidines (E(ox) < 1.3 V vs SCE, smoothly prepared from the corresponding aldehydes) have been herein employed for the successful release of tertiary, α-oxy, and α-amido radicals under photo-organo redox catalysis. The reaction relies on the unprecedented C–C cleavage occurring from the radical cation of these heterocyclic derivatives. Such a protocol is applied to the visible-light-driven conjugate radical addition onto Michael acceptors and vinyl (hetero)arenes under mild metal-free conditions.
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spelling pubmed-95529672022-10-12 Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines Luguera Ruiz, Adrián La Mantia, Marta Merli, Daniele Protti, Stefano Fagnoni, Maurizio ACS Catal [Image: see text] There is an urgent need to develop uncharged radical precursors to be activated under mild photocatalyzed conditions. 2-Substituted-1,3-oxazolidines (E(ox) < 1.3 V vs SCE, smoothly prepared from the corresponding aldehydes) have been herein employed for the successful release of tertiary, α-oxy, and α-amido radicals under photo-organo redox catalysis. The reaction relies on the unprecedented C–C cleavage occurring from the radical cation of these heterocyclic derivatives. Such a protocol is applied to the visible-light-driven conjugate radical addition onto Michael acceptors and vinyl (hetero)arenes under mild metal-free conditions. American Chemical Society 2022-09-29 2022-10-07 /pmc/articles/PMC9552967/ /pubmed/36249874 http://dx.doi.org/10.1021/acscatal.2c03768 Text en © 2022 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 Luguera Ruiz, Adrián
La Mantia, Marta
Merli, Daniele
Protti, Stefano
Fagnoni, Maurizio
Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines
title Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines
title_full Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines
title_fullStr Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines
title_full_unstemmed Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines
title_short Alkyl Radical Generation via C–C Bond Cleavage in 2-Substituted Oxazolidines
title_sort alkyl radical generation via c–c bond cleavage in 2-substituted oxazolidines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552967/
https://www.ncbi.nlm.nih.gov/pubmed/36249874
http://dx.doi.org/10.1021/acscatal.2c03768
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