Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology
Michael addition reactions of aldehyde to β-nitrostyrene catalyzed by L-proline were investigated by using controlled, monomode microwave-assisted technique in a closed vessel system. Ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim]NTf2) was used as the reaction med...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis
2014
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| Online Access: | http://psasir.upm.edu.my/id/eprint/34775/1/Optimization%20of%20microwave-assisted%20Michael%20addition%20reaction%20catalyzed%20by%20L-proline%20in%20ionic%20liquid%20medium%20using%20response%20surface%20methodology.pdf |
| _version_ | 1796972573095886848 |
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| author | Omar, Emmy Maryati Abdul Rahman, Mohd Basyaruddin Abd. Malek, Emilia Tejo, Bimo Ario Ni, Bukuo Headley, Allan D. |
| author_facet | Omar, Emmy Maryati Abdul Rahman, Mohd Basyaruddin Abd. Malek, Emilia Tejo, Bimo Ario Ni, Bukuo Headley, Allan D. |
| author_sort | Omar, Emmy Maryati |
| collection | UPM |
| description | Michael addition reactions of aldehyde to β-nitrostyrene catalyzed by L-proline were investigated by using controlled, monomode microwave-assisted technique in a closed vessel system. Ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim]NTf2) was used as the reaction medium to replace the commonly used volatile organic solvents and as a good absorbing solvent during Michael reaction under the influence of microwave irradiation. The Michael product is clean and generates good yields in short reaction times with moderate results on enantioselectivity (ee). In this work, optimization of proline-catalyzed Michael reaction was carried out using response surface methodology (RSM) based on a three-factor-three-level central composite design (CCD). Various reaction parameters including catalyst loading (5–30 mol%), reaction time (5–40 min), and substrate (2–5 equivalent ratio) were investigated. A high Michael yield (96.5%) with 36.9 ee% was obtained at the optimum conditions of 10.0 mol% catalyst loading, 5.0 min reaction time, and 2.0 substrate equivalent ratio. |
| first_indexed | 2024-03-06T08:30:00Z |
| format | Article |
| id | upm.eprints-34775 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T08:30:00Z |
| publishDate | 2014 |
| publisher | Taylor & Francis |
| record_format | dspace |
| spelling | upm.eprints-347752016-09-02T06:22:05Z http://psasir.upm.edu.my/id/eprint/34775/ Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology Omar, Emmy Maryati Abdul Rahman, Mohd Basyaruddin Abd. Malek, Emilia Tejo, Bimo Ario Ni, Bukuo Headley, Allan D. Michael addition reactions of aldehyde to β-nitrostyrene catalyzed by L-proline were investigated by using controlled, monomode microwave-assisted technique in a closed vessel system. Ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim]NTf2) was used as the reaction medium to replace the commonly used volatile organic solvents and as a good absorbing solvent during Michael reaction under the influence of microwave irradiation. The Michael product is clean and generates good yields in short reaction times with moderate results on enantioselectivity (ee). In this work, optimization of proline-catalyzed Michael reaction was carried out using response surface methodology (RSM) based on a three-factor-three-level central composite design (CCD). Various reaction parameters including catalyst loading (5–30 mol%), reaction time (5–40 min), and substrate (2–5 equivalent ratio) were investigated. A high Michael yield (96.5%) with 36.9 ee% was obtained at the optimum conditions of 10.0 mol% catalyst loading, 5.0 min reaction time, and 2.0 substrate equivalent ratio. Taylor & Francis 2014 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/34775/1/Optimization%20of%20microwave-assisted%20Michael%20addition%20reaction%20catalyzed%20by%20L-proline%20in%20ionic%20liquid%20medium%20using%20response%20surface%20methodology.pdf Omar, Emmy Maryati and Abdul Rahman, Mohd Basyaruddin and Abd. Malek, Emilia and Tejo, Bimo Ario and Ni, Bukuo and Headley, Allan D. (2014) Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology. Synthetic Communications, 44 (3). pp. 381-398. ISSN 0039-7911; ESSN: 1532-2432 http://www.tandfonline.com/doi/abs/10.1080/00397911.2013.808348 10.1080/00397911.2013.808348 |
| spellingShingle | Omar, Emmy Maryati Abdul Rahman, Mohd Basyaruddin Abd. Malek, Emilia Tejo, Bimo Ario Ni, Bukuo Headley, Allan D. Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology |
| title | Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology |
| title_full | Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology |
| title_fullStr | Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology |
| title_full_unstemmed | Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology |
| title_short | Optimization of microwave-assisted Michael addition reaction catalyzed by L-proline in ionic liquid medium using response surface methodology |
| title_sort | optimization of microwave assisted michael addition reaction catalyzed by l proline in ionic liquid medium using response surface methodology |
| url | http://psasir.upm.edu.my/id/eprint/34775/1/Optimization%20of%20microwave-assisted%20Michael%20addition%20reaction%20catalyzed%20by%20L-proline%20in%20ionic%20liquid%20medium%20using%20response%20surface%20methodology.pdf |
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