Organic-inorganic hybrid silica material derived from a monosilylated Grubbs-Hoveyda ruthenium carbene as a recyclable metathesis catalyst

Molecules

Volumn 15, Issue 8, 2010, Pages 5756-5767

  Borja, Guadalupe ^a   Pleixats, Roser ^a   Alibés, Ramón ^a   Cattoën, Xavier ^b   Chi Man, Michel Wong ^b  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b INSTITUT CHARLES GERHARDT   (France)

Author keywords

Catalyst immobilization; Organic inorganic hybrid material; Ring closing metathesis; Ruthenium alkylidene; Sol gel process

Indexed keywords

CARBENE; DRUG DERIVATIVE; METHANE; NITROGEN; ORGANIC COMPOUND; RUTHENIUM; SILICON DIOXIDE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; CYCLIZATION; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POROSITY; SYNTHESIS; TEMPERATURE;

CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MICROWAVES; MODELS, CHEMICAL; NITROGEN; ORGANIC CHEMICALS; POROSITY; RUTHENIUM; SILICON DIOXIDE; TEMPERATURE;

EID: 77956112979     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15085756     Document Type: Article

References (43)

1. Grubbs, R.H., Ed. Handbook of Metathesis, 1st ed.; Wiley-VCH: Weinheim, Germany, 2003; Volume 1-3.
2. Armstrong, S.K. Ring Closing Diene Metathesis in Organic Synthesis. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
3. Fürstner, A. Olefin Metathesis and Beyond. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
4. Deshmukh, P.H.; Blechert, S. Alkene metathesis: the search for better catalysts. Dalton Trans. 2007, 2479-2491.
5. Samojlowicz, C.; Bieniek, M.; Grela, K. Ruthenium-Based Olefin Metathesis Catalysts Bearing N-Heterocyclic Carbene Ligands. Chem. Rev. 2009, 109, 3708-3742.
6. Deiters, A.; Martin, S.F. Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring- Closing Metathesis. Chem. Rev. 2004, 104, 2199-2238.
7. McReynolds, M.D.; Dougherty, J.M.; Hanson, P.R. Synthesis of Phosphorus and Sulfur Heterocycles via Ring-Closing Olefin Metathesis. Chem. Rev. 2004, 104, 2239-2258.
8. Gradillas, A.; Pérez-Castells, J. Macrocyclization by Ring-Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations. Angew. Chem. Int. Ed. 2006, 45, 6086-6101.
9. Kotha, S.; Lahiri, K. Synthesis of Diverse Polycyclic Compounds via Catalytic Metathesis. Synlett 2007, 2767-2784.
10. Colacino, E.; Martinez, J.; Lamaty, F. Preparation of NHC-Ruthenium Complexes and their Catalytic Activity in Metathesis Reaction. Coord. Chem. Rev. 2007, 251, 726-764.
11. Donohoe, T.J.; Fishlock, L.P.; Procopiou, P.A. Ring-Closing Metathesis: Novel Routes to Aromatic Heterocycles. Chem. Eur. J. 2008, 14, 5716-5726.
12. Van Otterlo, W.A.L.; De Koning, C.B. Metathesis in the Synthesis of Aromatic Compounds. Chem. Rev. 2009, 109, 3743-3782.
13. Poulsen, C.S.; Madsen, R. Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes. Synthesis 2003, 1-18.
14. Diver, S.T.; Giessert, A.J. Enyne Metathesis (Enyne Bond Reorganization). Chem. Rev. 2004, 104, 1317-1382.
15. Mori, M. Ruthenium-Catalyzed ROM, RCM and CM of enyne. J. Mol. Catal. A: Chem. 2004, 213, 73-79.
16. Hansen, E.C.; Lee, D. Search for Solutions to the Reactivity and Selectivity Problems in Enyne Metathesis. Acc. Chem. Res. 2006, 39, 509-519.
17. Villar, H.; Frings, M.; Bolm, C. Ring Closing Enyne Metathesis: A Powerful Tool for the Synthesis of Heterocycles. Chem. Soc. Rev. 2007, 36, 55-66.
18. Diver, S.T. Ruthenium Vinyl Carbene Intermediates in Enyne Metathesis. Coord. Chem. Rev. 2007, 251, 671-701.
19. Mori, M. Synthesis of Natural Products and Related Compounds Using Enyne Metathesis. Adv. Synth. Catal. 2007, 349, 121-135.
20. Scholl, M.; Ding, S.; Lee, C.W., Grubbs, R.H. Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5- dihydroimidazol-2-ylidene Ligands. Org. Lett. 1999, 1, 953-956.
21. Kingsbury, J.S.; Harrity, J.P.A.; Bonitatebus, P.J., Jr; Hoveyda, A.H. A Recyclable Ru-Based Metathesis Catalyst. J. Am. Chem. Soc. 1999, 121, 791-799.
22. Garber, S.B.; Kingsbury, J.S.; Gray, B.L.; Hoveyda, A.H. Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts. J. Am. Chem. Soc. 2000, 122, 8168-8179.
23. Buchmeiser, M.R. Recent Advances in the Synthesis of Supported Metathesis Catalysts. New J. Chem. 2004, 28, 549-557.
24. Copéret, C.; Basset, J.-M. Strategies to Immobilize Well-Defined Olefin Metathesis Catalysts: Supported Homogeneous Catalysis vs. Surface Organometallic Chemistry. Adv. Synth. Catal. 2007, 349, 78-92.
25. Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S.P. Sustainable Concepts in Olefin Metathesis. Angew. Chem. Int. Ed. 2007, 46, 6786-6801.
26. Buchmeiser, M.R. Polymer-Supported Well-Defined Metathesis Catalysts. Chem. Rev. 2009, 109, 303-321.
27. Hoveyda, A.H.; Gillingham, D.G.; Van Veldhuizen, J.J.; Kataoka, O.; Garber, S.B.; Kingsbury, J.S.; Harrity, J.P.A. Ru Complexes Bearing Bidentate Carbenes: from Innocent Curiosity to Uniquely Effective Catalysts for Olefin Metathesis. Org. Biomol. Chem. 2004, 2, 8-23.
28. Karamé, I.; Boualleg, M.; Camus, J.-M.; Maishal, T.K.; Alauzun, J.; Basset, J.-M.; Copéret, C.; Corriu, R.J.P.; Jeanneau, E.; Mehdi, A.; Reyé, C.; Veyre, L.; Thieuleux, C. Tailored Ru-NHC Heterogeneous Catalysts for Alkene Metathesis. Chem. Eur. J. 2009, 15, 11820-11823.
29. Allen, D.P.; Van Wingerden, M.M.; Grubbs, R.H. Well-Defined Silica Supported Olefin Metathesis Catalysts. Org. Lett. 2009, 11, 1261-1264.
30. Zamboulis, A.; Moitra, N.; Moreau, J.J.E.; Cattoën, X.; Wong Chi Man, M. Hybrid materials: versatile matrices for supporting homogeneous catalysts. J. Mater. Chem. 2010, doi: 10.1039/c000334d.
31. Brinker, C.J.; Scherer, G.W. Sol-Gel Science; Academic: London, UK, 1990.
32. Shea, K.J.; Moreau, J.J.E.; Loy, D.; Corriu, R.J.P.; Boury, B. Functional Hybrid Materials; Gómez-Romero, P., Sanchez, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p. 50.
33. Moreau, J.J.E.; Wong Chi Man, M. The Design of Selective Catalysts from Hybrid Silica-Based Materials. Coord. Chem. Rev. 1998, 178-180, 1073-1084.
34. Elias, X.; Pleixats, R.; Wong Chi Man, M.; Moreau, J.J.E. Hybrid-Bridged Silsesquioxane as Recyclable Metathesis Catalyst Derived from a Bis-Silylated Hoveyda-Type Ligand. Adv. Synth. Catal. 2006, 348, 751-762.
35. Elias, X.; Pleixats, R.; Wong Chi Man, M.; Moreau, J.J.E. Hybrid Organic-Inorganic Materials Derived from a Monosilylated Hoveyda-Type Ligand as Recyclable Diene and Enyne Metathesis Catalysts. Adv. Synth. Catal. 2007, 349, 1701-1713.
36. Elias, X.; Pleixats, R.; Wong Chi Man, M. Hybrid Silica Materials Derived from Hoveyda-Grubbs Ruthenium Carbenes. Electronic Effects of the Nitro Group on the Activity and Recyclability as Diene and Enyne Metathesis Catalysts. Tetrahedron 2008, 64, 6770-6781.
37. Solans-Montfort, X.; Pleixats, R.; Sodupe, M. DFT Mechanistic Study on Diene Metathesis Catalyzed by Ru-Based Grubbs-Hoveyda Carbenes: The Key Role of π-Electron Density Delocalization in the Hoveyda Ligand. Chem. Eur. J. 2010, 16, 7331-7343.
38. Coquerel, Y.; Rodriguez, J. Microwave-Assisted Olefin Metathesis. Eur. J. Org. Chem. 2008, 1125-1132.
39. Nicks, F.; Borguet, Y.; Delfosse, S.; Bicchielli, D.; Delaude, L.; Sauvage, X.; Demonceau, A. Microwave-Assisted Ruthenium-Catalyzed Reactions. Aust. J. Chem. 2009, 62, 184-207.
40. Schmidt, B. Catalysis at the Interface of Ruthenium Carbene and Ruthenium Hydride Chemistry: Organometallic Aspects and Applications to Organic Synthesis. Eur. J. Org. Chem. 2004, 1865-1880.
41. Polarz, S.; Völker, B.; Jeremias, F. Metathesis Catalysts in Confining Reaction Fields- Confinement Effects vs. Surface Effects. Dalton Trans. 2010, 39, 577-584.
42. Burtscher, D.; Grela, K. Aqueous Olefin Metathesis. Angew. Chem. Int. Ed. 2009, 48, 442-454.
43. Hongfa, C.; Tian, J.; Bazzi, H.S.; Bergbreiter, D.E. Heptane-Soluble Ring-Closing Metathesis Catalysts. Org. Lett. 2007, 9, 3259-3261.