Back
 MRC  Vol.3 No.1 , January 2014
One-Pot Synthesis of Aldol Adduct Catalyzed by Immobilized Picolylamine on Zirconia
Abstract: Direct aldol reactions have been successfully performed using aromatic aldehyde and cyclic ketone in nonpolar solvent by using immobilized picolylamine on zirconia as a catalyst, in a double walled batch reactor. The prepared catalyst was characterized by SEM, XRD and FT-IR. FT-IR peaks reveal the presence of picolylamine on the surface of zirconia. The catalyst shows excellent catalytic activity in aldol reaction of cyclohexanone with benzaldehyde in cyclohexane giving 2-hydroxyphenylmethylcyclohexanone (55.7% yield) in 4 hr at 80?C. Furthermore, the catalyst is recoverable by simple filtration and could be used several times without significant loss in activity.
Cite this paper: M. Sadiq, R.  , M. Umar and G. Zamin, "One-Pot Synthesis of Aldol Adduct Catalyzed by Immobilized Picolylamine on Zirconia," Modern Research in Catalysis, Vol. 3 No. 1, 2014, pp. 1-5. doi: 10.4236/mrc.2014.31001.
References

[1]   Modern Aldol Reactions, Vols. 1 & 2 (Ed.:R. Mahrwald), Wiley-VCH, Weinheim 2004.

[2]   B. List, R. A. Lerner and C. F. Barbas III, “Proline-Catalyzed Direct Asymmetric Aldol Reactions,” Journal of the American Chemical Society, Vol. 122, No. 10, 2000, pp. 2395-2396. http://dx.doi.org/10.1021/ja994280y

[3]   B. List, “Proline-Catalyzed Asymmetric Reactions,” Tetrahedron, Vol. 58, No. 28, 2002, pp. 5573-5590.
http://dx.doi.org/10.1016/S0040-4020(02)00516-1

[4]   E. R. Jarvo and S. J. Miller, “Amino Acids and Peptides as Asymmetric Organo Catalysts,” Tetrahedron, Vol. 58, No. 13, 2002, pp. 2481-2495.
http://dx.doi.org/10.1016/S0040-4020(02)00122-9

[5]   W. Notz, F. Tanaka and C. F. Barbas III, “Enamine-Based Organocatalysis with Proline and Diamines: The Development of Direct Catalytic Asymmetric Aldol, Mannich, and Diels-Alder Reactions,” Accounts of Chemical Research, Vol. 37, No. 8, 2004, pp. 580-591.
http://dx.doi.org/10.1021/ar0300468

[6]   N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka and C. F. Barbas, “Organocatalytic Direct Asymmetric Aldol Reactions,” Journal of the American Chemical Society, Vol. 128, No. 3, 2006, pp. 734-735.
http://dx.doi.org/10.1021/ja0573312

[7]   Y. Hayashi, “In Water or in the Presence of Water?” Angewandte Chemie International Edition, Vol. 45, No. 48, 2006, pp. 8103-8104.
http://dx.doi.org/10.1002/anie.200603378

[8]   F. Cozzi, “Immobilization of Organic Catalysts,” Advanced Synthesis & Catalysis, Vol. 348, No. 12-13, 2006, pp. 1367-1390. http://dx.doi.org/10.1002/adsc.200606096

[9]   M. Benaglia, A. Puglisi and F. Cozzi, “Polymer-Supported Organic Catalysts,” Chemical Reviews, Vol. 103, No. 9, 2003, pp. 3401-34029.
http://dx.doi.org/10.1021/cr010440o

[10]   A. Corma and H. Garcia, “Silica-Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis,” Advanced Synthesis & Catalysis, Vol. 348, No. 12-13, 2006, pp. 1391-1412.
http://dx.doi.org/10.1002/adsc.200606192

 
 
Top