Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts
Dynamic kinetic resolution (DKR) is one of the most attractive routes to enantioselective synthesis, and ruthenium complexes are often applied as racemization catalysts. Two substituted cyclopentadienyl ruthenium complexes were immobilized covalently and non-covalently on mesoporous silica of mesoce...
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MDPI AG
2021-02-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/11/3/316 |
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| author | Monika Heba Dominika Stradomska Katarzyna Szymańska Andrzej Jarzębski Krzysztof Ambroziak Monika Masternak Anna Kolanowska Wojciech Pudło Nikodem Kuźnik |
| author_facet | Monika Heba Dominika Stradomska Katarzyna Szymańska Andrzej Jarzębski Krzysztof Ambroziak Monika Masternak Anna Kolanowska Wojciech Pudło Nikodem Kuźnik |
| author_sort | Monika Heba |
| collection | DOAJ |
| description | Dynamic kinetic resolution (DKR) is one of the most attractive routes to enantioselective synthesis, and ruthenium complexes are often applied as racemization catalysts. Two substituted cyclopentadienyl ruthenium complexes were immobilized covalently and non-covalently on mesoporous silica of mesocellular foam (MCF) and Santa Barbara Amorphous (SBA)-15 type functionalized with a 3 carbon spacer and 4-(chloromethyl)-N-amidobenzoate moiety. The catalysts were studied in a model reaction of secondary alcohol racemization. The immobilization decreased catalyst activity, considerably more for SBA-15 than for MCFs, and complete racemization of 1-phenylethanol was achieved within 24 h with the MCF-supported catalyst. The catalyst could be recovered and reused, thus paving the way for further development of the DKR process. The synthesized materials were fully characterized by Fourier-transform infrared spectroscopy analysis, thermogravimetry analysis, inductively cou-pled plasma optical emission spectrometry, and nitrogen adsorption at 77 K. |
| first_indexed | 2024-03-09T06:14:25Z |
| format | Article |
| id | doaj.art-2471675e91324ace8824961c9d4317b8 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-09T06:14:25Z |
| publishDate | 2021-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-2471675e91324ace8824961c9d4317b82023-12-03T11:55:07ZengMDPI AGCatalysts2073-43442021-02-0111331610.3390/catal11030316Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization CatalystsMonika Heba0Dominika Stradomska1Katarzyna Szymańska2Andrzej Jarzębski3Krzysztof Ambroziak4Monika Masternak5Anna Kolanowska6Wojciech Pudło7Nikodem Kuźnik8Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Engineering, Silesian University of Technology, M. Strzody 7, 44-100 Gliwice, PolandDepartment of Chemical Engineering, Silesian University of Technology, M. Strzody 7, 44-100 Gliwice, PolandDepartment of Chemical Engineering, Silesian University of Technology, M. Strzody 7, 44-100 Gliwice, PolandIntermag Sp. z o.o., Olkusz, Al. 1000-lecia 15G, 32-300 Olkusz, PolandIntermag Sp. z o.o., Olkusz, Al. 1000-lecia 15G, 32-300 Olkusz, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Engineering, Silesian University of Technology, M. Strzody 7, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDynamic kinetic resolution (DKR) is one of the most attractive routes to enantioselective synthesis, and ruthenium complexes are often applied as racemization catalysts. Two substituted cyclopentadienyl ruthenium complexes were immobilized covalently and non-covalently on mesoporous silica of mesocellular foam (MCF) and Santa Barbara Amorphous (SBA)-15 type functionalized with a 3 carbon spacer and 4-(chloromethyl)-N-amidobenzoate moiety. The catalysts were studied in a model reaction of secondary alcohol racemization. The immobilization decreased catalyst activity, considerably more for SBA-15 than for MCFs, and complete racemization of 1-phenylethanol was achieved within 24 h with the MCF-supported catalyst. The catalyst could be recovered and reused, thus paving the way for further development of the DKR process. The synthesized materials were fully characterized by Fourier-transform infrared spectroscopy analysis, thermogravimetry analysis, inductively cou-pled plasma optical emission spectrometry, and nitrogen adsorption at 77 K.https://www.mdpi.com/2073-4344/11/3/316ruthenium complexesracemizationchiral secondary alcoholsresolution of enantiomers |
| spellingShingle | Monika Heba Dominika Stradomska Katarzyna Szymańska Andrzej Jarzębski Krzysztof Ambroziak Monika Masternak Anna Kolanowska Wojciech Pudło Nikodem Kuźnik Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts Catalysts ruthenium complexes racemization chiral secondary alcohols resolution of enantiomers |
| title | Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts |
| title_full | Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts |
| title_fullStr | Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts |
| title_full_unstemmed | Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts |
| title_short | Engineering and Performance of Ruthenium Complexes Immobilized on Mesoporous Siliceous Materials as Racemization Catalysts |
| title_sort | engineering and performance of ruthenium complexes immobilized on mesoporous siliceous materials as racemization catalysts |
| topic | ruthenium complexes racemization chiral secondary alcohols resolution of enantiomers |
| url | https://www.mdpi.com/2073-4344/11/3/316 |
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