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]BF4) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds of...
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| Format: | Article |
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MDPI AG
2017-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/9/1385 |
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| author | Mosadegh Keshavarz Amanollah Zarei Ahmady Azar Mostoufi Neda Mohtasham |
| author_facet | Mosadegh Keshavarz Amanollah Zarei Ahmady Azar Mostoufi Neda Mohtasham |
| author_sort | Mosadegh Keshavarz |
| collection | DOAJ |
| description | In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF4) 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]BF4 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. |
| first_indexed | 2024-12-10T06:20:32Z |
| format | Article |
| id | doaj.art-0f1c324c00c54badb4cf2d4143a70d44 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T06:20:32Z |
| publishDate | 2017-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0f1c324c00c54badb4cf2d4143a70d442022-12-22T01:59:20ZengMDPI AGMolecules1420-30492017-08-01229138510.3390/molecules22091385molecules22091385One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free CatalystMosadegh Keshavarz0Amanollah Zarei Ahmady1Azar Mostoufi2Neda Mohtasham3Department of Gas and Petroleum, Yasouj University, Gachsaran 75918-74831, IranMarine Pharmaceutical Science Research Center, Ahvaz JundiShapur University of Medical Sciences, Ahvaz 14536-33143, IranDepartment of Medicinal Chemistry, Ahvaz Jundishapur University of Medical Sciences, Ahvaz 14536-33143, IranPediatric Division, Abuzar Children’s Medical Center, Ahvaz Jundishapur University of Medical Sciences, Ahvaz 14536-33143, IranIn a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF4) 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]BF4 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.https://www.mdpi.com/1420-3049/22/9/1385γ-lactoneflourous ionic liquidone-pot synthesiscatalystregioselective |
| spellingShingle | Mosadegh Keshavarz Amanollah Zarei Ahmady Azar Mostoufi Neda Mohtasham 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 Molecules γ-lactone flourous ionic liquid one-pot synthesis catalyst regioselective |
| 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 | γ-lactone flourous ionic liquid one-pot synthesis catalyst regioselective |
| url | https://www.mdpi.com/1420-3049/22/9/1385 |
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