Silica Immobilized Second Generation Hoveyda-Grubbs: A Convenient, Recyclable and Storageable Heterogeneous Solid Catalyst
The second generation Hoveyda–Grubbs metathesis catalyst was successfully immobilized on silica in pellet and powder form following a practical and fast synthesis procedure. The activity of the solid system is truly heterogeneous, efficient in various metathesis reaction types and stable for at leas...
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| Veröffentlicht in: | Advanced synthesis & catalysis Jg. 350; H. 13; S. 1949 - 1953 |
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| Sprache: | Englisch |
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Weinheim
WILEY-VCH Verlag
05.09.2008
WILEY‐VCH Verlag |
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| ISSN: | 1615-4150, 1615-4169 |
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| Abstract | The second generation Hoveyda–Grubbs metathesis catalyst was successfully immobilized on silica in pellet and powder form following a practical and fast synthesis procedure. The activity of the solid system is truly heterogeneous, efficient in various metathesis reaction types and stable for at least 4000 TON. Ru contamination of the products was very low (ppb levels). The successful use of the robust system has been demonstrated in a continuous reactor set‐up. |
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| AbstractList | The second generation Hoveyda–Grubbs metathesis catalyst was successfully immobilized on silica in pellet and powder form following a practical and fast synthesis procedure. The activity of the solid system is truly heterogeneous, efficient in various metathesis reaction types and stable for at least 4000 TON. Ru contamination of the products was very low (ppb levels). The successful use of the robust system has been demonstrated in a continuous reactor set‐up. |
| Author | Sels, Bert F. Houthoofd, Kristof Van Berlo, Boris Jacobs, Pierre A. |
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| References_xml | – reference: A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity, Org. Biomol. Chem. 2004, 2, 8-23; – reference: S. T. Nguyen, R. H. Grubbs, J. Organomet. Chem. 1995, 497, 195-200; – reference: J. C. Conrad, H. H. Parnas, J. L. Snelgrove, D. E. Fogg, J. Am. Chem. Soc. 2005, 127, 11882-11883. – reference: X. Elias, R. Pleixats, M. W. Chi Man, J. J. E. Moreau, Adv. Synth. Catal. 2006, 348, 751-762; – reference: R. R. Schrock, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 4592-4633. – reference: T. S. Halbach, S. Mix, D. Fischer, S. Maechling, J. O. Krause, C. Sievers, S. Blechert, O. Nuyken, M. R. Buchmeiser, J. Org. Chem. 2005, 70, 4687-4694; – reference: T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; – reference: C. Copéret, J.-M. Basset, Adv. Synth. Catal. 2007, 349, 78-92; – reference: J. Lim, S. S. Lee, S. N. Riduan, J. Y. Yinga, Adv. Synth. Catal. 2007, 349, 1066-1076; – reference: R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; – reference: F. Michalek, D. Mädge, J. Rühe, W. Bannwarth, J. Organomet. Chem. 2006, 691, 5172. – reference: J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 791-799; – reference: R. H. Grubbs, Handbook of Metathesis, Vol. 1, Wiley-VCH, Weinheim, 2003, pp 61-67. – reference: J. O. Krause, O. Nuyken, K. Wurst, M. R. Buchmeiser, Chem. Eur. J. 2004, 10, 777-784; – reference: F. Michalek, W. Bannwarth, Helv. Chim. Acta 2006, 89, 1030-1037; – reference: L. Li, J.-L. Shi, Adv. Synth. Catal. 2005, 347, 1745-1749; – reference: D. E. De Vos, M. Dams, B. F. Sels, P. A. Jacobs, Chem. Rev. 2002, 102, 3615-3640. – reference: A. Michrowska, K. Mennecke, U. Kunz, A. Kirschning, K. Grela, J. Am. Chem. Soc. 2006, 128, 13261-13267; – reference: X. Elias, R. Pleixats, M. W. C. Man, J. J. E. Moreau, Adv. Synth. Catal. 2006, 348, 751; – reference: Q. Yao, Y. Zhang, Angew. Chem. Int. Ed. 2003, 42, 3395-3398; – reference: H. Clavier, K. Grela, A. Kirschning, M. Mauduit, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 6786-6801. – start-page: 2 year: 2004 end-page: 23 publication-title: Org. Biomol. Chem. – start-page: 497 year: 1995 end-page: 200 publication-title: J. Organomet. Chem. – start-page: 89 year: 2006 end-page: 1037 publication-title: Helv. Chim. Acta – start-page: 128 year: 2006 end-page: 13267 publication-title: J. Am. Chem. Soc. – start-page: 70 year: 2005 end-page: 4694 publication-title: J. Org. Chem. – start-page: 34 year: 2001 end-page: 29 publication-title: Acc. Chem. Res. – start-page: 102 year: 2002 end-page: 3640 publication-title: Chem. Rev. – start-page: 61 year: 2003 end-page: 67 – start-page: 349 year: 2007 end-page: 1076 publication-title: Adv. Synth. Catal. – start-page: 46 year: 2007 end-page: 6801 publication-title: Angew. Chem. Int. Ed. – start-page: 42 year: 2003 end-page: 3398 publication-title: Angew. Chem. Int. 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| SubjectTerms | heterogeneous catalysis immobilization metathesis N-heterocyclic carbenes ring-opening polymerization ruthenium |
| Title | Silica Immobilized Second Generation Hoveyda-Grubbs: A Convenient, Recyclable and Storageable Heterogeneous Solid Catalyst |
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