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One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst

In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF(4)) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds...

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Autores principales: Keshavarz, Mosadegh, Zarei Ahmady, Amanollah, Mostoufi, Azar, Mohtasham, Neda
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151549/
https://www.ncbi.nlm.nih.gov/pubmed/28846652
http://dx.doi.org/10.3390/molecules22091385
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author Keshavarz, Mosadegh
Zarei Ahmady, Amanollah
Mostoufi, Azar
Mohtasham, Neda
author_facet Keshavarz, Mosadegh
Zarei Ahmady, Amanollah
Mostoufi, Azar
Mohtasham, Neda
author_sort Keshavarz, Mosadegh
collection PubMed
description In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF(4)) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds of the desired γ-lactones were directly prepared with high regioselectivities and yields in a simple one-pot procedure using [DMIM]F as Si–O bond activator and [Hbim]BF(4) as solvent and acidic ionic liquid catalyst. The ionic liquid mixture was recovered and reused three times and no loss in its activity was observed.
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spelling pubmed-61515492018-11-13 One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst Keshavarz, Mosadegh Zarei Ahmady, Amanollah Mostoufi, Azar Mohtasham, Neda Molecules Article In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF(4)) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds of the desired γ-lactones were directly prepared with high regioselectivities and yields in a simple one-pot procedure using [DMIM]F as Si–O bond activator and [Hbim]BF(4) as solvent and acidic ionic liquid catalyst. The ionic liquid mixture was recovered and reused three times and no loss in its activity was observed. MDPI 2017-08-28 /pmc/articles/PMC6151549/ /pubmed/28846652 http://dx.doi.org/10.3390/molecules22091385 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Keshavarz, Mosadegh
Zarei Ahmady, Amanollah
Mostoufi, Azar
Mohtasham, Neda
One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst
title One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst
title_full One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst
title_fullStr One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst
title_full_unstemmed One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst
title_short One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst
title_sort one-pot green regioselesctive synthesis of γ-lactones from epoxides and ketene silyl acetals using 1,3-dimethylimidazolium fluoride as a recoverable metal-free catalyst
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151549/
https://www.ncbi.nlm.nih.gov/pubmed/28846652
http://dx.doi.org/10.3390/molecules22091385
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