One-pot synthesis of recyclable palladium catalysts for hydrogenations and carbon-carbon coupling reactions

Tetrahedron Letters

Volumn 45, Issue 38, 2004, Pages 7057-7059

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

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

Author keywords

C C coupling reactions; Catalysts; Hydrogenation; Nanomaterial; Pd; Sol gel process

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; CARBON; ETHYLENE GLYCOL; NANOPARTICLE; PALLADIUM; SILICON DIOXIDE; TETRAKIS(TRIPHENYLPORPHINE)PALLADIUM; TETRAMETHOXYSILANE; TITANIUM; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; CYCLIZATION; HECK REACTION; HYDROGENATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; SONOGASHIRA REACTION; STILLE REACTION; SUZUKI REACTION; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 4444383970     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.126     Document Type: Article

References (30)

1. E.-I. Negishi E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis 2002 John Wiley & Sons New York
2. Y.M.A. Yamada, K. Takeda, H. Takahashi, and S. Ikegami Tetrahedron 60 2004 4097
3. J.W. Byun, and Y.S. Lee Tetrahedron Lett. 45 2004 1837
4. A. Biffis, M. Zecca, and M. Basato J. Mol. Catal. A: Chem. 173 2001 249
5. F. Zhao, B.M. Bhanage, M. Shirai, and M. Arai Chem. Eur. J. 6 2000 843
6. B.M. Bhanage, S. Fujita, T. Yoshida, Y. Sano, and M. Arai Tetrahedron Lett. 44 2003 3505
7. S.W. Kim, M. Kim, W.Y. Lee, and T. Hyeon J. Am. Chem. Soc. 124 2002 5990
8. S. Tanaka, F. Mizukami, S. Niwa, M. Toba, K. Maeda, H. Shimada, and K. Kunimori Appl. Catal., A: General 229 2002 165
9. B.M. Choudary, N.S. Chowdari, K. Jyothi, N.S. Kumar, and M.L. Kantam Chem. Commun. 2002 586
10. M.T. Reetz, and E. Westermann Angew. Chem., Int. Ed. 39 2000 165
11. C. Pham-Huu, N. Keller, L.J. Charbonniere, R. Ziessel, and M.J. Ledoux Chem. Commun. 2000 1871
12. Y. Li, X.M. Hong, D.M. Collard, and M.A. El-Sayed Org. Lett. 2 2000 2385
13. Z. Kiraly, B. Veisz, A. Mastalir, Z. Razga, and I. Dekany Chem. Commun. 1999 1925
14. B.F.G. Johnson Coord. Chem. Rev. 190 1999 1269
15. C.P. Mehnert, D.W. Weaver, and J.Y. Ying J. Am. Chem. Soc. 120 1998 12289
16. M.T. Reetz, R. Breinbauer, and K. Wanninger Tetrahedron Lett. 37 1996 4499
17. A. Roucoux, J. Schulz, and H. Patin Chem. Rev. 102 2002 3757
18. G. Schmid, and L.F. Chi Adv. Mater. 10 1998 515
19. R. Akiyama, and S. Kobayashi J. Am. Chem. Soc. 125 2003 3412
20. K. Okamoto, R. Akiyama, and S. Kobayashi J. Org. Chem. 69 2004 2871
21. S. Yu, K. Yao, S. Shannigrahi, and F.T.E. Hock J. Mater. Res. 18 2003 737
22. H.Y. Jung, R.K. Gupta, D.W. Seo, Y.H. Kim, and C.M. Whang Bull. Korean Chem. Soc. 23 2002 884
23. L. Hench, and J.K. West Chem. Rev. 90 1990 33
24. For a recent review for the solâ€"gel processed catalysts see: Z.-I. Lu, E. Lindner, and H.A. Mayer Chem. Rev. 102 2002 3543
25. 1H NMR in the filtrate
26. The inductively coupled plasma (ICP) analysis revealed that the palladium contents of 1 and 2 are 0.59 and 0.79 wt %, respectively, and that palladium is entrapped in the catalysts in more than 95% yields
27. n 550: 29%)
28. 4 did not increase the activity
29. The palladium on charcoal would cause ignition when it is exposed to air after the use under hydrogen
30. In the filtrate palladium was not detected by ICP analysis