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http://dx.doi.org/10.7464/ksct.2011.17.1.013

Synthesis of Palladium Nanoparticles Encapsulated in Phosphine Ligand-Grafted Mesoporous Silicas and Their Application to Suzuki Cross-Coupling Reaction  

Kim, Sang-Wook (Department of Molecular Science and Technology, Ajou University)
Joo, Jin (Department of Applied Chemistry, Kyungpook National University)
Publication Information
Clean Technology / v.17, no.1, 2011 , pp. 13-18 More about this Journal
Abstract
Phosphine ligand-grafted mesoporous silica materials with large pores were prepared for the ligand-modified heterogeneous Pd nanocatalysts. New heterogeneous catalytic system was developed using palladium nanoparticles encapsulated in phosphine ligand-grafted mesoporous silica. The catalyst showed good catalytic activities for Suzuki cross-coupling using bromobenzene derivatives due to excellent phosphine ligand effects. Catalytic results showed nanoparticie catalysts can be recycled twice with decreased yields.
Keywords
Mesoporous silica; Pd nanoparticlcs; Suzuki cross-coupling reaction;
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1 Sullivan, J. A., Flanagan, K. A., and Hain, H., "Suzuki coupling activity of an aqueous phase Pd nanoparticle dispersion and a carbon nanotube/Pd nanoparticle composite," Catal. Today, 145(1-2), 108-113 (2009).   DOI
2 Ellis, P. J., Fairlamb, I. J. S., Hackett, S. F. J., Wilson, K., and Lee, A. F., "Evidence for the Surface-Catalyzed Suzuki- Miyaura Reaction over Palladium Nanoparticles: An Operando XAS Study," Angew. Chem. Int. Ed., 122(10), 1864-1868 (2010).   DOI   ScienceOn
3 Suzuki, A., "Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995- 1998," J. Organomet. Chem., 576(1-2), 147-168 (1999).   DOI   ScienceOn
4 Kim, S. -W., Kim, M., Lee, W. Y., and Hyeon, T., "Fabrication of hollow palladium spheres and their successful application to the recyclable heterogeneous catalyst for suzuki coupling reactions," J. Am. Chem. Soc., 124(26), 7642-7643 (2002).   DOI   ScienceOn
5 Bedford, R. B., Singh, U. G., Walton, R. I., Williams, R. T., and Davis, S. A., "Nanoparticulate Palladium Supported by Covalently Modified Silicas: Synthesis, Characterization, and Application as Catalysts for the Suzuki Coupling of Aryl Halides," Chem. Mater., 17(4), 701-707 (2005).   DOI   ScienceOn
6 Kim, S. -S., Pauly, T. R., and Pinnavaia, T. J., "Non-ionic surfactant assembly of ordered, very large pore molecular sieve silicas from water soluble silicates," Chem. Commun., 36(17), 1661-1662 (2000).
7 Gao, R. H., and Angelici, R. J., "Combination Catalysts Consisting of a Homogeneous Catalyst Tethered to a Silica-Supported Palladium Heterogeneous Catalyst: Arene Hydrogenation," J. Am. Chem. Soc., 119(29), 6937-6938 (1997).   DOI   ScienceOn
8 Weddle, K. S., Aikin, J. D., and Finke, R. G., "Rh(0) Nanoclusters in Benzene Hydrogenation Catalysis: Kinetic and Mechanistic Evidence that a Putative $[(C_8H_{17})_3NCH_3]^+$$[RhCl_4]^-$ Ion- Pair Catalyst Is Actually a Distribution of $Cl^-$ and $[(C_8H_{17})_3 NCH_3]^+$ Stabilized Rh(0) Nanoclusters," J. Am. Chem. Soc., 120(23), 5653-5666 (1998).   DOI   ScienceOn
9 Reetz, M. T., and Westermann, E., "Phosphane-Free Palladium- Catalyzed Coupling Reactions: The Decisive Role of Pd Nanoparticles," Angew. Chem. Int. Ed., 39(1), 165-168 (2000).   DOI   ScienceOn
10 Li, Y., Hong, X. M., Collard, D. M., and El-Sayed, M. A., "Suzuki cross-coupling reactions catalyzed by palladium nanoparticles in aqueous solution," Org. Lett., 2(15), 2385-2388 (2000).   DOI   ScienceOn
11 Son, S. U., Lee, S. I., Chung, Y. K., Kim, S.-W., and Hyeon, T., "The First Intramolecular Pauson-Khand Reaction in Water Using Aqueous Colloidal Cobalt Nanoparticles as Catalysts," Org. Lett., 4(2), 277-279 (2002).   DOI   ScienceOn
12 Bae, S. J., Kim, S. -W., Hyeon, T., and Kim, B. M., "New chiral heterogeneous catalysts based on mesoporous silica: Asymmetric diethylzinc addition to benzaldehyde," Chem. Commun., 31-32 (2000).
13 Miyaura, N., and Suzuki, A., "Palladium-Catalyzed Cross- Coupling Reactions of Organoboron Compounds," Chem. Rev., 95(7), 2457-2483 (1995).   DOI   ScienceOn
14 Kim, S.-W., Park, J., Jang, Y., Chung, Y., Hwang, S., and Hyeon, T., "Synthesis of Monodisperse Palladium Nanoparticles," Nano Lett., 3(9), 1289-1291 (2003).   DOI   ScienceOn
15 Kim, S. -W., Bae, S. J., Hyeon, T., and Kim, B. M., "Chiral proline-derivative anchored on mesoporous silicas and their application to the asymmetric diethylzinc addition to benzaldehyde," Micropor. Mesopor. Mater., 44-45, 523-529 (2001).   DOI
16 Kim, S.-W., Son, S. U., Lee, S. S., Hyeon, T., and Chung, Y. K., "Colloidal cobalt nanoparticles: a highly active and reusable Pauson-Khand catalyst," Chem. Commun., 37(21), 2212-2123 (2001).
17 Klingelhofer, W. H., Greiner, A., Oestreich, S., Forster, S., and Antoniettie, M., "Preparation of Palladium Colloids in Block Copolymer Micelles and Their Use for the Catalysis of the Heck Reaction," J. Am. Chem. Soc., 119(42), 10116-10120 (1997).   DOI   ScienceOn
18 Ertl, G., Knozinger, H., and Weitkamp, J., Handbook of Heterogeneous Catalysis, Wiley-VCH, Weinheim, 1997.
19 Kim, W., Kim D., Hong, Y., Kang, T., and Yi, J., "Hydrogen Storage Using Pd Doped Mesoporous Carbon Materials," Clean Technology, 12(2), 107-111 (2006).
20 Jiang, Y., and Gao, Q., "Heterogeneous Hydrogenation Catalyses over Recyclable Pd(0) Nanoparticle Catalysts Stabilized by PAMAM-SBA-15 Organic-Inorganic Hybrid Composites," J. Am. Chem. Soc., 128(3), 716-717 (2005).
21 Mayer, A. B. R., Mark, J. E., and Morris, R. E., "Palladium and Platinum Nanocatalysts Protected by Amphiphilic Block Copolymers," Polym. J., 30(3), 197-205 (1998).   DOI   ScienceOn
22 Toshima, N., Shiraishi, Y., Teranishi, T., Miyake, M., Tominaga, T., Watanabe, H., Brijoux, W., Bonnemann, H., and Schmid, G., "Various ligand-stabilized metal nanoclusters as homogeneous and heterogeneous catalysts in the liquid phase," Appl. Organomet. Chem., 15(3), 178-196 (2001).   DOI   ScienceOn
23 Bonnemann, H., Brijoux, W., Siepen, K., Hormes, J., Franke, R., Pollmann, J., and Rothe, J., "Surfactant stabilized palladium colloids as precursors for cis-selective alkyne-hydrogenation catalysts," Appl. Organomet. Chem., 11(10-11), 783-796 (1997).   DOI   ScienceOn
24 Chen, C. W., Serizawa, T., and Akashi, M., "Preparation of Platinum Colloids on Polystyrene Nanospheres and Their Catalytic Properties in Hydrogenation," Chem. Mater., 11(5), 1381-1389 (1999).   DOI   ScienceOn
25 Baiker, A., "Chiral catalysis on solids," Curr. Opin. Solid State Mater. Sci., 3(1), 86-93 (1998).   DOI   ScienceOn
26 Blaser, H., Baiker, A., and Prins, R., Heterogeneous Catalysis and Fine Chemicals IV, Elsevier, Amsterdam, 1997.
27 Clark, J. H., and Macquarrie, D. J., "Catalysis of liquid phase organic reactions using chemically modified mesoporous inorganic solids," Chem. Commun., 34(8), 853-860 (1998).