Palladium nanoparticles in polymers: Catalyst for alkene hydrogenation, carbon-carbon cross-coupling reactions, and aerobic alcohol oxidation

Synthesis

Volumn , Issue 22, 2006, Pages 3790-3794

  Cheon, Min Park ^a   Min, Serk Kwon ^a   Park, Jaiwook ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Cross coupling; Heterogeneous; Hydrogenation; Oxidations; Palladium; Polymer

Indexed keywords

CATALYSTS; HYDROGENATION; ORGANIC POLYMERS; OXIDATION; PALLADIUM COMPOUNDS; PHASE TRANSITIONS;

CARBON-CARBON CROSS-COUPLING REACTIONS; NANOPARTICLES; ORGANIC TRANSFORMATIONS; PALLADIUM CATALYST;

NANOSTRUCTURED MATERIALS;

ALCOHOL; ALKENE; ALKYNE; CARBON; PALLADIUM; POLYMER;

ALCOHOL OXIDATION; ARTICLE; CATALYST; CROSS COUPLING REACTION; HYDROGENATION; NANOPARTICLE; SYNTHESIS;

EID: 33845312957     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950329     Document Type: Article

References (42)

1. Negishi, E.-I. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
2. (a) Lysén, M.; Köhler, K. Synthesis 2006, 692.
3. (b) Shokouhimehr, M.; Kim, J.-H.; Lee, Y.-S. Synlett 2006, 618.
4. (c) He, H. S.; Yan, J. J.; Shen, R.; Zhuo, S.; Toy, P. H. Synlett 2006, 563.
5. (d) Uozumi, Y.; Kikuchi, M. Synlett 2005, 1775.
6. (e) Crudden, C. M.; Sateesh, M.; Lewis, R. J. Am. Chem. Soc. 2005, 127, 10045.
7. (f) Wang, Y.; Sauer, D. R. Org. Lett. 2005, 6, 2793.
8. (g) Motokura, K.; Fujita, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2005, 46, 5507.
9. (h) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Tetrahedron 2004, 60, 4097.
10. (i) Ramesh, C.; Nakamura, R.; Kubota, Y.; Miwa, M.; Sugi, Y. Synthesis 2003, 501.
11. (a) Koutsopoulos, S.; Johannessen, T.; Eriksen, K. M.; Fehrmann, R. J. Catal. 2006, 238, 206.
12. (b) Silvestre-Albero, J.; Rupprechter, G.; Freund, H. Chem. Commun. 2006, 80.
13. (c) Narayanan, R.; El-Sayed, M. A. J. Catal. 2005, 234, 348.
14. (d) Son, H. K.; Jang, Y.; Park, J.; Na, H. B.; Park, H. M.; Yun, H. J.; Lee, J.; Hyeon, T. J. Am. Chem. Soc. 2004, 126, 5026.
15. (e) Bhanage, B. M.; Fujita, S.; Yoshida, T.; Sano, Y.; Arai, M. Tetrahedron Lett. 2003, 44, 3505.
16. (f) Kim, S. W.; Kim, M.; Lee, W. Y.; Hyeon, T. J. Am. Chem. Soc. 2002, 124, 5990.
17. (g) Reetz, M. T.; Westermann, E. Angew. Chem. Int. Ed. 2000, 39, 165.
18. (h) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
19. (a) Chung, M.-K.; Schlaf, M. J. Am. Chem. Soc. 2004, 126, 7386.
20. (b) Roucoux, A.; Schulz, J.; Patin, H. Chem. Rev. 2002, 102, 3757.
21. (c) Schmid, G.; Chi, L. F. Adv. Mater. 1998, 10, 515.
22. (a) Hagio, H.; Sugiura, M.; Kobayashi, S. Org. Lett. 2006, 8, 375.
23. (b) Nishio, R.; Sugiura, M.; Kobayashi, S. Org. Lett. 2005, 7, 483.
24. (c) Okamoto, K.; Akiyama, R.; Yoshida, H.; Yoshida, T.; Kobayashi, S. J. Am. Chem. Soc. 2005, 127, 2125.
25. (d) Okamoto, K.; Akiyama, R.; Kobayashi, S. Org. Lett. 2004, 6, 1987.
26. (e) Okamoto, K.; Akiyama, R.; Kobayashi, S. J. Org. Chem. 2004, 69, 2871.
27. (f) Akiyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3412.
28. (a) Kim, W.-H.; Park, I. S.; Park, J. Org. Lett. 2006, 8, 2543.
29. (b) Kwon, M. S.; Kim, N.; Seo, S. H.; Park, I. S.; Cheedrala, R. K.; Park, J. Angew. Chem. Int. Ed. 2005, 44, 6913.
30. (c) Kwon, M. S.; Kim, N.; Park, C. M.; Lee, J. S.; Kang, K. Y.; Park, J. Org. Lett. 2005, 7, 1077.
31. (d) Park, I. S.; Kwon, M. S.; Kim, N.; Lee, J. S.; Kang, K. Y.; Park, J. Chem. Commun. 2005, 5667.
32. (e) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057.
33. 4 in a mixture of butan-1-ol and THF before the polymerization with AIBN.
34. (a) Chauhan, B. S.; Rathore, J.; Bandoo, T. J. Am. Chem. Soc. 2004, 126, 8493.
35. (b) Pillai, U. R.; Sahle-Demessie, E. J. Mol. Catal. A: Chem. 2004, 222, 153.
36. (c) Yoon, B.; Kim, H.; Wai, C. M. Chem. Commun. 2003, 1040.
37. (d) Berthold, H.; Schotten, T.; Honig, H. Synthesis 2002, 1607.
38. 3PO was recovered from the filtrate in more than 90% yield.
39. In the cases of butan-2-ol and tetra(ethylene glycol), the resulting catalysts showed 26% of the activity of 1 and 44%, respectively.
40. In the combinations of methacrylic acid and ethylene glycol dimethacrylate, methyl acrylate and ethylene glycol dimethacrylate, and acrylamide and 2,3-dimethylbuta-1,3-diene, the resulting catalysts showed 22% of the activity of 1, 34%, 3%, respectively.
41. 1H NMR spectroscopy, and Pd was not detected by ICP analysis.
42. 4 was entrapped in the catalyst.