Selective Reduction of C=O in α,β-Unsaturated Carbonyls through Catalytic Hydrogen Transfer Reaction over Mixed Metal Oxides

Synlett

Volumn , Issue 1, 2004, Pages 146-148

  Sonavane, Sachin U ^a   Jayaram, Radha V ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

Catalytic transfer hydrogenation; Liquid phase reaction; Mixed metal oxide; , unsaturated carbonyl compounds

Indexed keywords

2 PROPANOL; CARBON; CARBONYL DERIVATIVE; COBALT DERIVATIVE; HYDROGEN; METAL OXIDE; OXYGEN; POTASSIUM HYDROXIDE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; LIQUID; PROTON TRANSPORT; REDUCTION; SYNTHESIS;

EID: 0346340885     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43359     Document Type: Article

References (26)

1. Bartok, M.; Molnar, A. S. The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1997, Chap. 16, 844; and references cited therein.
2. Rylander, P. Catalytic Hydrogenation Over Platinum Metals; Academic press: New York, 1967.
3. Giroir-Fendler, A.; Richard, D.; Gallezot, P. Heterogeneous Catalysis and Fine Chemicals; Elsevier: Amsterdam, 1988, 171.
4. Hernandez, M.; Kalck, P. J. Mol. Catal. A: Chem. 1997, 116, 131.
5. Yamaguchi, M.; Natta, A.; Reddy, R. S.; Hirama, H. Synlett 1997, 117.
6. Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751.
7. Pauling, L. The Chemical Bond; Cornell University: USA, 1967.
8. Bradshaw, C. W.; Fu, H.; Shen, G.-J.; Wong, C.-H. J. Org. Chem. 1992, 57, 1526.
9. Ohkuma, T.; Ikchira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467.
10. Arase, A.; Hoshi, M.; Yamaki, T.; Nakauishi, H. J. Chem. Soc., Chem. Commun. 1994, 855.
11. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
12. Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129.
13. Brieger, G.; Nestrick, T. J. Chem. Rev. 1974, 74, 567.
14. Zassinolich, G.; Mestroni, G. Chem. Rev. 1992, 92, 1051.
15. Sonavane, S. U.; Jayaram, R. V. Synth. Commun. 2003, 33, 843.
16. Sonavane, S. U.; Mohopatra, S. K.; Jayaram, R. V.; Selvam, P. Chem. Lett. 2003, 32, 142.
17. Mohopatra, S. K.; Sonavane, S. U.; Jayaram, R. V.; Selvam, P. Tetrahedron Lett. 2002, 43, 8527.
18. Mohopatra, S. K.; Sonavane, S. U.; Jayaram, R. V.; Selvam, P. Org. Lett. 2002, 24, 4297.
19. Mohopatra, S. K.; Sonavane, S. U.; Jayaram, R. V.; Selvam, P. Appl. Cat., B: Environmental 2003, in press.
20. Hubat, R.; Daage, M.; Bonnelle, J. P. Appl. Cat. 1986, 22, 231.
21. Nitta, Y.; Ueno, K.; Imanaka, T. Appl. Cat. 1989, 56, 9.
22. Kumbhar, P. S.; Coq, B.; Moreau, C.; Moreau, P.; Planiex, J. M.; Warawadekar, M. G. Catalysis: Modern Trends 1995, 541.
23. 3 solution under vigorous stirring until pH 10.0 was achieved. Then the co-precipitated hydroxides were washed repeatedly to get neutral filtrate free of the anions precursor materials. The precipitate was then dried in an air oven for 24 h at 383 K and ground below 100 mesh. The hydroxide was then calcined in a muffle furnace at 773 K for 8 h.
24. -1. Optical microscopy photography indicates the presence of uniform particle size, which is found to be 45 μm.
25. Typical Experimental Procedure: The liquid phase reaction was carried out in a 100 mL two-necked round bottom flask equipped with a reflux condenser and a thermometer. In a typical catalytic hydrogen transfer reaction, KOH pellets (20 mmol) were dissolved in propan-2-ol (20 mL) to which the substrate (20 mmol) was added along with 130 mg catalyst, which was then heated at reflux at 356 K for a few hours depending upon the nature of the substrate.
26. For checking the reusability, after the first reaction, the catalyst was recovered by simple filtration, and washed several times with acetone followed by thorough washing with water to remove alkali, and further dried at 373 K for 1 h and then the reaction was repeated for the subsequent cycles.