Magnetically separable base catalysts: Heterogeneous catalysis vs. quasi-homogeneous catalysis

Applied Sciences (Switzerland)

Volumn 2, Issue 2, 2012, Pages 260-276

  Abu Reziq, Raed ^a   Alper, Howard ^b  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Base catalysis; Heterogeneous catalysis; Magnetic nanoparticles; Quasi homogeneous catalysis; Sol gel chemistry

Indexed keywords

EID: 84892166438     PISSN: None     EISSN: 20763417     Source Type: Journal    
DOI: 10.3390/app2020260     Document Type: Article

References (59)

1. Recoverable and Recyclable Catalysts; Benaglia, M., Ed.; John Wiley & Sons: Chichester, UK, 2009
2. Lu, Z.; Lindner, E.; Mayer, H.A. Applications of sol-gel-processed interphase catalysts. Chem. Rev. 2002, 102, 3543-3578
3. Marr, A.C.; Marr, P.C. Entrapping homogeneous catalysts by sol-gel methods: The bottom-up synthesis of catalysts that recycle and cascade. Dalton Trans. 2011, 40, 20-26
4. 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, 20, 9322-9338
5. Ciriminna, R.; Demma Carà, P.; Sciortino, M.; Pagliaro, M. Catalysis with doped sol-gel silicates. Adv. Synth. Catal. 2011, 353, 677-687
6. Ciriminna, R.; Pagliaro, M. Recent uses of sol-gel doped catalysts in the fine chemicals and pharmaceutical industry. Org. Process Res. Dev. 2006, 10, 320-326
7. Schätz, A.; Reiser, O.; Stark, W.J. Nanoparticles as semi-heterogeneous catalyst supports. Chem. Eur. J. 2010, 16, 8950-8967
8. Astruc, D.; Lu. F.; Aranzaes, J.R. Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2005, 44, 7852-7872
9. Gupta, A.K.; Curtis, A.S.G. Surface modified superparamagnetic nanoparticles for drug delivery: Interaction studies with human fibroblasts in culture. J. Mater. Sci. Mater. Med. 2004, 15, 493-496
10. Neuberger, T.; Schoepf, B.; Hofmann, H.; Hofmann, M.; von Rechenberg, B. Superparamagnetic nanoparticles for biomedical applications: possibilities and limitations of a new drug delivery system. J. Magn. Magn. Mater. 2005, 293, 483-496
11. Pankhurst, Q.A.; Connolly, J.; Jones, S.K.; Dobson, J. Applications of magnetic nanoparticles in biomedicine. J. Phys. D: Appl. Phys. 2003, 36, R167-R181
12. Perez, J.M.; Simeone, F.J.; Saeki, Y.; Josephson, L.; Weissleder, R. Viral-induced self-assembly of magnetic nanoparticles allows the detection of viral particles in biological media. J. Am. Chem. Soc. 2003, 125, 10192-10193
13. Graham, D.L.; Ferreira H.A.; Freitas, P.P. Magnetoresistive-based biosensors and biochips. Trends Biotechnol. 2004, 22, 455-462
14. 3 beads-CdSe/ZnS quantum dots core-Shell nanocomposite particles for cell separation. Nano Lett. 2004, 4, 409-413
15. Xu, C.; Xu, K.; Gu, H.; Zheng, R.; Liu, H.; Zhang, X. Guo, Z.; Xu, B. Dopamine as a robust anchor to immobilize functional molecules on the iron oxide shell of magnetic nanoparticles. J. Am. Chem. Soc. 2004, 126, 9938-9939
16. Hiergeist, R.; Andra, W.; Buske, N.; Hergt, R.; Hilger, I.; Richter, U.; Kaiser, W. Application of magnetite ferrofluids for hyperthermia. J. Magn. Magn. Mater. 1999, 201, 420-422
17. Jordan, A.; Scholz, R.; Wust, P.; Fahling, H.; Felix, R. Magnetic fluid hyperthermia (MFH): Cancer treatment with AC magnetic field induced excitation of biocompatible superparamagnetic nanoparticles. J. Magn. Magn. Mater. 1999, 201, 413-419
18. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.M. Magnetically recoverable nanocatalysts. Chem. Rev. 2011, 111, 3036-3075
19. Shyles, S.; Schünemann, V.; Thiel, W.R. Magnetically separable nanocatalysts: Bridges between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2010, 49, 3428-3459
20. Zhu, Y.; Stubbs, L.P.; Ho, F.; Liu, R.; Ship, C.P.; Maguire, J.A.; Hosmane, N.S. Magnetic nanocomposites: A new perspective in catalysis. ChemCatChem 2010, 2, 365-374
21. Polshettiwar, V.; Varma, R.S. Green chemistry by nano-catalysis. Green Chem. 2010, 12, 743-754
22. Kawamura, M.; Sato, K. Magnetically separable phase-transfer catalysts. Chem. Commun. 2006, 4718-4719
23. Lee, D.; Lee, J.; Lee, H.; Jin, S.; Hyeon, T.; Kim, B.M. Filtration-free recyclable catalytic asymmetric dihydroxylation using a ligand immobilized on magnetic mesocellular mesoporous silica. Adv. Synth. Catal. 2006, 348, 41-46
24. Luo, S.; Zheng, X.; Xu, H.; Mi, X.; Zhang, L.; Cheng, J.P. Magnetic nanoparticle-supported Morita-Baylis-Hillman catalysts. Adv. Synth. Catal. 2007, 349, 2431-2434
25. Dálaigh, C.ó.; Corr, S.A.; Gun'ko, Y.; Connon, S.J. A magnetic-nanoparticle-supported 4-N,N-dialkylaminopyridine catalyst: Excellent reactivity combined with facile catalyst recovery and recyclability. Angew. Chem. Int. Ed. 2007, 46, 4329-4332
26. Luo, S.; Zheng, X.; Cheng, J.-P. Asymmetric bifunctional primary aminocatalysis on magnetic nanoparticles. Chem. Commun. 2008, 5719-5721
27. Schätz, A.; Grass, R.N.; Stark, W.J.J.; Reiser, O. TEMPO supported on magnetic C/Co-nanoparticles: A highly active and recyclable organocatalyst. Chem. Eur. J. 2008, 14, 8262-8266
28. Gleeson, O.; Tekoriute, R.; Gun'ko, Y.K.; Connon, S.J. The first magnetic nanoparticle-supported chiral DMAP analogue: Highly enantioselective acylation and excellent recyclability. Chem. Eur. J. 2009, 15, 5669-5673
29. Wang, B.G.; Ma, B.C.; Wang, Q.; Wang, W. Superparamagnetic nanoparticle-supported (S)-diphenyl-prolinol trimethylsilyl ether as a recyclable catalyst for asymmetric Michael addition in water. Adv. Synth. Catal. 2010, 352, 2923-2928
30. Polshettiwar, V.; Baruwati, B.; Varma, R.S. Magnetic nanoparticle-supported glutathione: A conceptually sustainable organocatalyst. Chem. Commun. 2009, 1837-1839
31. Polshettiwar, V.; Varma, R.S. Nano-organocatalyst: Magnetically retrievable ferrite-anchored glutathione for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis. Tetrahedron 2010, 66, 1091-1097
32. Riente, P.; Mendoza, C.; Pericás, M.A. Functionalization of Fe3O4 magnetic nanoparticles for organocatalytic Michael reactions. J. Mater. Chem. 2011, 21, 7350-7355
33. Abu-Reziq, R.; Alper, H.; Wang, D.; Post, M.L. Metal supported on dendronized magnetic nanoparticles: Highly selective hydroformylation catalysts. J. Am. Chem. Soc. 2006, 128, 5279-5282
34. Abu-Reziq, R.; Wang, D.; Post, M.L.; Alper, H. Platinum nanoparticles supported on ionic liquid-modified magnetic nanoparticles: Selective hydrogenation catalysts. Adv. Synth. Catal. 2007, 349, 2145-2150
35. Abu-Reziq, R.; Wang, D.; Post, M.L. Alper, H. Separable catalysts in one-pot syntheses for greener chemistry. Chem. Mater. 2008, 20, 2544-2550
36. Jones, G. The Knoevenagel condensation. Org. React. 1967, 15, 204-599
37. Barret, A.G.M.; Graboski, G.G. Conjugated nitroalkenes: Versatile intermediates in organic synthesis. Chem. Rev. 1986, 86, 751-762
38. Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A. One-pot synthesis of 1,3-dinitroalkanes under heterogeneous catalysis. Synthesis, 2004, 1938-1940
39. Kantam, M.L.; Choudary, B.M.; Reddy, C.V.; Rao, K.K.; Figueras, F. Aldol and Knoevenagel condensations catalysed by modified Mg-Al hydrotalcite: A solid base as catalyst useful in synthetic organic chemistry. Chem Commun. 1998, 1033-1034
40. Bulbule, V.J.; Deshpande, V.H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V.T. Heterogeneous Henry reaction of aldehydes: Diastereoselective synthesis of nitroalcohol derivatives over Mg-Al hydrotalcites. Tetrahedron 1999, 55, 9325-9332
41. Akutu, K.; Kabashima, H.; Seki, T.; Hattori, H. Nitroaldol reaction over solid base catalysts. Appl. Catal. A 2003, 247, 65-74
42. Khan, F.A.; Dash, J.; Satapathy, R.; Upadhyay, S.K. Hydrotalcite catalysis in ionic liquid medium: A recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation. Tetraheron Lett. 2004, 45, 3055-3058
43. Choudary, B.M.; Kantam, M.L.; Reddy, C.V.; Rao, K.K.; Figueras, F. Henry reactions catalysed by modified Mg-Al hydrotalcite: An efficient reusable solid base for selective synthesis of beta-nitroalkanols. Green Chem. 1999, 187-189
44. Saito, T.; Goto, H.; Honda, K.; Fujii, T.T. Acid-base catalysts derived from weakly acidic ion-exchange resin: Efficiency in the Knoevenagel condensation. Tetrahedron Lett. 1992, 33, 7535-7538
45. Hein, R.W.; Astle, M.J.; Shelton, J.R. Ion-exchange Resin Catalysis of the Knoevenagel Condensation of Ketones. J. Org. Chem. 1961, 26, 4874-4878
46. Ballini, R.; Bosica, G.; Forconi, P. Nitroaldol (Henry) reaction catalyzed by Amberlyst A-21 as a far superior heterogeneous catalyst. Tetrahedron 1996, 52, 1677-1684
47. Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Amino-groups immobilized on silica-gel-An efficient reusable heterogeneous catalyst for the Knoevenagel condensation. J. Chem. Soc., Perkin Trans. 1 1989, 105-107
48. Ballini, R.; Bosica, G.; Livi, D.; Palmieri, A.; Maggi, R.; Sartori, G. Use of heterogeneous catalyst KG-60-NEt2 in Michael and Henry reactions involving nitroalkanes. Tetrahedron Lett. 2003, 44, 2271-2273
49. Corma, A.; Fornes, V.; Martin-Aranda, R.M.; Garcia, H.; Primo, J. Zeolite as base catalysts-Condensation of aldehydes with derivatives of malonic esters. Appl. Catal. 1990, 59, 237-248
50. Kubota, Y.; Nishizaki, Y.; Ikeya, H.; Saeki, M.; Hida, T.; Kawazu, S.; Yoshida, M.; Fujii, H.; Sugi, Y. Organic-silicate hybrid catalysts based on various defined structures for Knoevenagel condensation. Micropor. Mesopor. Mater. 2004, 70, 135-149
51. Jaenicke, S.; Chuah, G.K.; Lin, X.H.; Hu, X.C. Organic-inorganic hybrid catalysts for acid-and base-catalyzed reactions. Micropor. Mesopor. Mater. 2000, 35-36, 143-153
52. Inaki, Y.; Kajita, Y.; Yoshida, H.; Ito, K.; Hattori, T. New basic mesoporous silica catalyst obtained by ammonia grafting. Chem. Commun. 2001, 2358-2359
53. Huh, S.; Chen, H.-T.; Wiench, J.W.; Pruski, M.; Lin, V.S.-Y. Controlling the selectivity of competitive nitroaldol condensation by using a bifunctionalized mesoporous silica nanosphere-based catalytic system. J. Am.Chem. Soc. 2004, 126, 1010-1011
54. Rodriguez, I.; Iborra, S.; Corma, A.; Rey, F.; Jordá, J.L. MCM-41-Quaternary organic tetraalkylammonium hydroxide composites as strong and stable Bronsted base catalysts. Chem. Commun. 1999, 593-594
55. Phan, N.T.S.; Jones, C.W. Highly accessible catalytic sites on recyclable organosilanefunctionalized magnetic nanoparticles: An alternative to functionalized porous silica catalysts. J. Mol. Catal. A: Chem. 2006, 253, 123-131
56. 3 nanocrystallites: An efficient magnetic and recyclable heterogeneous catalyst for aqueous Knoevenagel condensation. J. Mol. Catal. A: Chem. 2009, 306, 107-112
57. Gill, C.G.; Long, W.; Jones, C.W. Magnetic nanoparticle polymer brush catalysts: Alternative hybrid organic/inorganic structures to obtain high, local catalyst loadings for use in organic transformations. Catal. Lett. 2009, 131, 425-431
58. Gao, Z.; Zhou, J.; Cui, F.; Zhu, Y.; Hua, Z.; Shi, J. Superparamagnetic mesoporous Mg-Fe bi-metal oxides as efficient magnetic solid-base catalysts for Knoevenagel condensations. Dalton Trans. 2010, 39, 11132-11135
59. Senapati, K. K.; Borgohain, C.; Phukan P. Synthesis of highly stable CoFe2O4 nanoparticles and their use as magnetically separable catalyst for Knoevenagel reaction in aqueous medium. J. Mol. Catal. A: Chem. 2011, 339, 24-31