Convenient deoxygenation of aromatic ketones by silica-supported chitosan schiff base palladium catalyst

Synthetic Communications

Volumn 42, Issue 4, 2012, Pages 574-581

  Gong, S W ^a   He, H F ^a   Zhao, Ch Q ^a   Liu, L J ^a   Cui, Q X ^a  

^a LIAOCHENG UNIVERSITY   (China)

Author keywords

Aromatic ketones; Chitosan support; Hydrogenation; Palladium catalyst

Indexed keywords

ACETOPHENONE; CARBONYL DERIVATIVE; CHITOSAN; ETHYLBENZENE; HYDROCARBON; HYDROGEN; KETONE; PALLADIUM; SCHIFF BASE; SILICON DIOXIDE;

ARTICLE; CATALYST; DEOXYGENATION; ENVIRONMENTAL TEMPERATURE; HYDROGENATION; HYDROGENOLYSIS; PRESSURE; REACTION TIME;

EID: 80054717994     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.527423     Document Type: Article

References (27)

1. Reeves, W. P.; Murry, J. A.; Willoughby, D. W.; Friedrich, W. J. Clemmensen reductions using ultrasonic irradiation. Synth. Commun. 1988, 18, 1961-1966.
2. Huang, M. L. A simple modification of the Wolff-Kishner reduction. J. Am. Chem. Soc. 1946, 68, 2487-2488.
3. Szmant, H. H.; Harmuth, C. M. The Wolff-Kishner reaction of hydrazones. J. Am. Chem. Soc. 1964, 86, 2909-2914.
4. Suzuki, H.; Masuda, R.; Kubota, H.; Osuka, A. Selective reduction with lithium aluminum hydride/diphosphorus tetraiodide: A mild conversion of aromatic ketones to parent hydrocarbons. Chem. Lett. 1983, 6, 909-910.
5. Ono, A.; Maruyama, T.; Suzuki, N. Hydrogenation of diaryl and arylalkyl ketones by sodium borohydride and aluminum chloride. Synth. Commun. 1987, 17, 1001-1005.
6. Nightingale, D.; Radford, H. D. The hydrogenation of aromatic ketones with hydrogen and copper-chromium oxide catalyst. J. Org. Chem. 1949, 14, 1089-1093.
7. Glebov, L. S.; Mikaya, A. I.; Yatsenko, A. E.; Zaikin, V. G.; Kliger, G. A.; Loktev, S. M. Effective gas-phase deoxygenation of alcohols and ketones on iron catalyst. Tetrahedron Lett. 1985, 26, 3373-3376.
8. Maier, W. F.; Bergmann, K.; Bleicher, W.; Schleyer, P. V. Heterogeneous deoxygenation of ketones. Tetrahedron Lett. 1981, 22, 4227-4230.
9. 2 catalyst. J. Mol. Catal. A: Chem. 2002, 187, 277-281.
10. Lavaud, N.; Magnoux, P.; Alvarez, F.; Melo, L.; Giannetto, G.; Guisnet, M. Transformation of acetophenone over Pd HFAU catalysts-Reaction scheme. J. Mol. Catal. A: Chem. 1999, 142, 223-236.
11. Magnoux, P.; Lavaud, N.; Guisnet, M. Transformation of acetophenone over Pd aluminosilicate catalysts: Influence of acidity and pore structure. Top. Catal. 2000, 13, 291-299.
12. Van Doorslaer, C.; Wahlen, J.; Mertens, P. G. N.; Thijs, B.; Nockemann, P.; Binnemans, K.; De Vos, D. E. Catalytic hydrogenolysis of aromatic ketones in mixed choline- betainium ionic liquids. Chem. Sus. Chem. 2008, 1, 997-1005.
13. Hardy, J.J.E.; Hubert, S.; Macquarrie, D. J.; Wilson, A. Chitosan-based heterogeneous catalysts for Suzuki and Heck reactions. J. Green Chem. 2004, 6, 53-56.
14. Yamada, M.; Maeda, A. Heteropolyacid-conjugated chitosan matrix for triphase catalyst. Polymer 2009, 50, 6076-6082.
15. Burkhardt, A.; Görls, H.; Plass, W. Nickel(II) complexes with Schiff base ligands derived from epimeric pyranose backbones as 2,3-chelators: Modeling the coordination chemistry of chitosan. Carbohydr. Res. 2008, 343, 1266-1277.
16. Guibal, E. Heterogeneous catalysis on chitosan-based materials: A review. Prog. Polym. Sci. 2005, 30, 71-109.
17. Vincent, T.; Peirano, F.; Guibal, E. Chitosan-supported palladium catalyst, VI: Nitroaniline degradation. J. Appl. Polym. Sci. 2004, 94, 1634-1642.
18. Blondet, F. P.; Vincent, T.; Guibal, E. Hydrogenation of nitrotoluene using palladium supported on chitosan hollow fiber: Catalyst characterization and influence of operative parameters studied by experimental design methodology. Int. J. Biol. Macromol. 2008, 43, 69-78.
19. Peirano, F.; Vincent, T.; Quignard, F.; Robitzer, M.; Guibal, E. Palladium supported on chitosan hollow fiber for nitrotoluene hydrogenation. J. Membrane Sci. 2009, 329, 30-45.
20. Vincent, T.; Guibal, E. Chitosan-supported palladium catalyst, 3: Influence of experimental parameters on nitrophenol degradation. Langmuir 2003, 19, 8475-8483.
21. Han, H. S.; Jiang, S. N.; Huang, M. Y.; Jiang, Y. Y. Catalytic hydrogenation of aromatic nitro compounds by non-noble metal complexes of chitosan. Polym. Adv. Technol. 1996, 7, 704-706.
22. Vincent, T.; Spinelli, S.; Guibal, E. Chitosan-supported palladium catalyst, II: Chlorophenol dehalogenation. Ind. Eng. Chem. Res. 2003, 42, 5968-5976.
23. Adlim, M.; Bakar, M. A.; Liew, K. Y.; Ismail, J. Synthesis of chitosan-stabilized platinum and palladium nanoparticles and their hydrogenation activity. J. Mol. Catal. A: Chem. 2004, 212, 141-149.
24. Yin, M. Y.; Yuan, G. L.; Wu, Y. Q.; Huang, M. Y.; Jiang, Y. Y. Asymmetric hydrogenation of ketones catalyzed by a silica-supported chitosan-palladium complex. J. Mol. Cat. A: Chem. 1999, 147, 93-98.
25. Sun, Y. X.; Guo, Y.; Lu, Q. Z.; Meng, X. L.; Wu, X. H.; Guo, Y. L.; Wang, Y. S.; Liu, X. H.; Zhang, Z. G. Highly selective asymmetry transfer hydrogenation of prochiral acetophenone catalyzed by palladium-chitosan on silica. Catal. Lett. 2005, 100, 213-217.
26. dos Santos, J. E.; Dockala, E. R.; Cavalheiro, É . T. G. Synthesis and characterization of Schiff bases from chitosan and salicylaldehyde derivatives. Carbohydr. Polym. 2005, 60, 277-282.
27. 2-supported chitosan Schiff-Base palladium catalyst. Chin. J. Catal. 2010, 31, 846-850.