A PS-DES immobilized ruthenium carbene: A robust and easily recyclable catalyst for olefin metathesis

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9055-9059

  Grela, Karol ^a   Tryznowski, Mariusz ^b   Bieniek, Michał ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBENE; POLYSTYRENE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; RECYCLING;

EID: 0037049171     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02283-9     Document Type: Article

References (27)

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3. For approaches where ruthenium impurities are removed by addition of various scavengers, see: (a) Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 2000, 40, 4137-4140; (b) Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Mendez-Andino, J. Yang, J. Org. Lett. 2000, 2, 1259-1261; (c) Ahn, Y. M.; Yang, K.; Georg, G. I. Org. Lett. 2001, 3, 1411-1413.
4. For approaches where ruthenium impurities are removed by addition of various scavengers, see: (a) Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 2000, 40, 4137-4140; (b) Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Mendez-Andino, J. Yang, J. Org. Lett. 2000, 2, 1259-1261; (c) Ahn, Y. M.; Yang, K.; Georg, G. I. Org. Lett. 2001, 3, 1411-1413.
5. 2 as the reaction medium. The ruthenium carbenes 1a and 1c act as heterogenous catalysts in this environmentally benign medium: (a) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem., Int. Ed. 1997, 36, 2466-2469; (b) Fürstner, A.; Ackermann, L.; Beck, K.; Hori, H.; Koch, D.; Langemann, K.; Liebl, M.; Six, C.; Leitner W. J. Am. Chem. Soc. 2001, 123, 9000-9006.
6. 2 as the reaction medium. The ruthenium carbenes 1a and 1c act as heterogenous catalysts in this environmentally benign medium: (a) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem., Int. Ed. 1997, 36, 2466-2469; (b) Fürstner, A.; Ackermann, L.; Beck, K.; Hori, H.; Koch, D.; Langemann, K.; Liebl, M.; Six, C.; Leitner W. J. Am. Chem. Soc. 2001, 123, 9000-9006.
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25. 2 until the filtrate was clear (4×1 mL) affording 7 as dark green beads, showing loading of 0.22 mmol Ru/g (ICP-MS analysis). Samples of resin 7 (loadings of 0.22-0.35 mmol/g) did not lose activity after 3 months of storage in air at rt. General procedure for ICP-MS determination of Ru. A solution of TBAF (0.5 mL, 1 M in THF) was added to the resin 7 (20 mg). The mixture was stirred at rt for 2 h. The resin was filtered and washed with THF (4×2 mL) and MeOH (2×2 mL). The combined filtrate was analyzed by ICP-MS using standard procedure.
26. 26OSi 226.1753. Found: 226.1754.
27. Homoallylic alcohols 11g and 11j can be conveniently obtained, using poly(ethylene)-supported activated zinc (12), which has been developed in our laboratory: Makosza, M.; Nieczypor, P.; Grela, K. Tetrahedron 1998, 54, 10827-10836.