Highly efficient dehalogenation using hydroxyapatite-supported palladium nanocluster catalyst with molecular hydrogen

Green Chemistry

Volumn 6, Issue 10, 2004, Pages 507-509

  Hara, Takayoshi ^a   Mori, Kohsuke ^a   Oshiba, Michitaka ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CHLOROBENZENE; HALOPHENOL; HYDROGEN; HYDROXYAPATITE; ORGANOHALOGEN DERIVATIVE; PALLADIUM;

AQUEOUS SOLUTION; ARTICLE; ATMOSPHERE; CATALYST; CHEMICAL STRUCTURE; DEHALOGENATION; MOLECULE;

EID: 9144248339     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408185d     Document Type: Article

References (38)

1. (a) F. Alonso, I. P. Beletskaya and M. Yus, Chem. Rev., 2002, 102, 4009;
2. (b) V. V. Grushin and H. Alper, Chem. Rev., 1994, 94, 1047;
3. (c) A. R. Pinder, Synthesis, 1980, 425.
4. 2O, and HCl could not be achieved and the reactions are often accompanied with the formation of toxic halogenated chemicals such as dioxins, phosgene, and chlorine, see M. D. Erickson, S. E. Swanson, J. J. D. Flora Jr. and G. D. Hinshaw, Environ. Sci. Technol., 1989, 23, 462.
5. (a) C. Desmarrets, S. Kuhl, R. Schneider and Y. Fort, Organometallics, 2002, 21, 1554;
6. (b) M. S. Viciu, G. A. Grasa and S. P. Nolan, Organometallics, 2001, 20, 3607.
7. (a) R. E. Maleczka Jr., R. J. Rahaim Jr. and R. R. Teixeira, Tetrahedron Lett., 2002, 43, 7087;
8. (b) R. J. Rahaim Jr. and R. E. Maleczka Jr., Tetrahedron Lett., 2002, 43, 8823;
9. (c) R. Boukherroub, C. Chatgilialoglu and G. Manuel, Organometallics, 1996, 15, 1508.
10. R. Hara, K. Sato, W.-H. Sun and T. Takahashi, Chem. Commun., 1999, 845.
11. P. P. Cellier, J.-F. Spindler, M. Taillefer and H.-J. Cristau, Tetrahedron Lett., 2003, 44, 7191.
12. (a) M. A. Atienza, M. A. Esteruelas, M. Fernández, J. Herrero and M. Oliván, New J. Chem., 2001, 25, 775;
13. (b) I. Pri-Bar and O. Buchman, J. Org. Chem., 1986, 51, 734.
14. (a) I. Yamanaka, K. Nishikawa, S. Takenaka and K. Otsuka, Stud. Surf. Sci. Catal., 2003, 145, 383;
15. (b) N. Faucher, Y. Ambroise, J.-C. Cintrat, E. Doris, F. Pillon and B. Rousseau, J. Org. Chem., 2002, 67, 932;
16. (c) M. E. Cucullu, S. P. Nolan, T. R. Belderrain and R. H. Grubbs, Organometallics, 1999, 18, 1299;
17. (d) Y. Zhang, S. Liao and Y. Xu, Tetrahedron Lett., 1994, 35, 4599;
18. (e) D. T. Ferrughelli and I. T. Horváth, J. Chem. Soc., Chem. Commun., 1992, 806;
19. (f) C. A. Marques, M. Selva and P. Tundo, J. Org. Chem., 1993, 58, 5256;
20. (g) J. B. Hoke, G. A. Gramiccioni and E. N. Balko, Appl. Catal. B: Environ., 1992, 1, 285.
21. (a) K. Mori, T. Hara, T. Mizugaki, K. Ebitani and K. Kaneda, J. Am. Chem. Soc., 2003, 125, 11460;
22. (b) K. Mori, M. Tano, T. Mizugaki, K. Ebitani and K. Kaneda, New J. Chem., 2002, 26, 1536;
23. (c) K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani and K. Kaneda, Chem. Commun., 2001, 461;
24. (d) K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani and K. Kaneda, J. Am. Chem. Soc., 2000, 122, 7144.
25. (a) T. Hara, K. Mori, T. Mizugaki, K. Ebitani and K. Kaneda, Tetrahedron Lett., 2003, 44, 6207;
26. (b) M. Murata, T. Hara, K. Mori, M. Ooe, T. Mizugaki, K. Ebitani and K. Kaneda, Tetrahedron Lett., 2003, 44, 4981;
27. (c) K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani and K. Kaneda, J. Am. Chem. Soc., 2002, 124, 11572.
28. 1H-NMR spectra.
29. - to the active Pd species.
30. C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997.
31. K. A. Tuppurainen, P. H. Rrokojärvi, A. H. Asikainen, M. Aatamila and J. Ruuskanen, Environ. Sci. Technol., 2000, 34, 4958.
32. (a) V. Felis, C. D. Bellefon, P. Fouilloux and D. Schweich, Appl. Catal. B: Environ., 1999, 20, 91;
33. (b) C. Schuth and M. Reinhard, Appl. Catal. B: Environ., 1998, 18, 215.
34. (a) J. C. Elliott, Structure and Chemistry of the Apatites and Other Calcium Orthophosphates, Elsevier, Amsterdam, 1994;
35. (b) D. N. Misra, J. Adhes. Sci. Technol., 1994, 8, 87.
36. Addition of a radical trap, 2,2′,6,6′-tetramethylpiperidine N-oxyl (TEMPO), to the reaction medium hardly influenced the dehalogenation. This result indicates that the present dehalogenation does not proceed via the free radical pathway.
37. 3 showed formation of an equimolar amount of AgCl relative to the consumed substrate.
38. S. Sugiyama, T. Minami, H. Hayashi, M. Tanaka, N. Shigemoto and J. B. Moffat, J. Chem. Soc., Faraday Trans., 1996, 92, 293.