Clean Technology (청정기술)

The Korean Society of Clean Technology (한국청정기술학회)
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Synthesis of Palladium Nanoparticles Encapsulated in Phosphine Ligand-Grafted Mesoporous Silicas and Their Application to Suzuki Cross-Coupling Reaction

팔라듐 나노입자가 담지된 메조포러스 실리카의 제조와 이를 이용한 Suzuki Cross-Coupling 반응의 적용연구

  • Kim, Sang-Wook (Department of Molecular Science and Technology, Ajou University) ;
  • Joo, Jin (Department of Applied Chemistry, Kyungpook National University)
  • 김상욱 (아주대학교 분자과학기술학과) ;
  • 주진 (경북대학교 응용화학과)
  • Received : 2010.12.15
  • Accepted : 2011.03.24
  • Published : 2011.03.31
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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.

포스핀(phosphine) 리간드(ligand)가 도포된 메조포러스 실리카(mesoporous silicas)에 팔라듐 나노입자를 도입하여 새로운 팔라듐(Pd) 불균일 촉매(heterogeneous catalyst)를 제조하였다. 제조된 촉매는 브롬화벤젠 유도체(bromobenzene derivatives)들의 Suzuki cross-coupling 반응에 대하여 뛰어난 촉매활성을 나타내었고 촉매를 두 번째 사용하였을 때는 수율이 감소하였다.

Keywords

References

  1. Blaser, H., Baiker, A., and Prins, R., Heterogeneous Catalysis and Fine Chemicals IV, Elsevier, Amsterdam, 1997.
  2. 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).
  3. Baiker, A., "Chiral catalysis on solids," Curr. Opin. Solid State Mater. Sci., 3(1), 86-93 (1998). https://doi.org/10.1016/S1359-0286(98)80070-3
  4. Ertl, G., Knozinger, H., and Weitkamp, J., Handbook of Heterogeneous Catalysis, Wiley-VCH, Weinheim, 1997.
  5. 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). https://doi.org/10.1021/ja9714604
  6. 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). https://doi.org/10.1295/polymj.30.197
  7. 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). https://doi.org/10.1002/aoc.146
  8. 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). https://doi.org/10.1002/(SICI)1099-0739(199710/11)11:10/11<783::AID-AOC630>3.0.CO;2-#
  9. 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). https://doi.org/10.1021/cm9900047
  10. 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). https://doi.org/10.1021/ja9710058
  11. 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). https://doi.org/10.1021/ja973045h
  12. 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). https://doi.org/10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO;2-B
  13. 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). https://doi.org/10.1021/ol0061687
  14. 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).
  15. 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). https://doi.org/10.1021/ol017043k
  16. 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).
  17. 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).
  18. 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). https://doi.org/10.1021/cm048860s
  19. 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).
  20. 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). https://doi.org/10.1021/nl0343405
  21. 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). https://doi.org/10.1016/S1387-1811(01)00230-X
  22. 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).
  23. Miyaura, N., and Suzuki, A., "Palladium-Catalyzed Cross- Coupling Reactions of Organoboron Compounds," Chem. Rev., 95(7), 2457-2483 (1995). https://doi.org/10.1021/cr00039a007
  24. 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). https://doi.org/10.1016/S0022-328X(98)01055-9
  25. 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). https://doi.org/10.1021/ja026032z
  26. 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). https://doi.org/10.1016/j.cattod.2008.05.026
  27. 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). https://doi.org/10.1002/ange.200906675