Document Type: Original Research Article

Authors

Department of Chemistry, College of Sciences, University of Birjand, Birjand 97175-615, Iran

Abstract

Mn(II) salen complex immobilized on nano silicagel was prepared by incorporating Mn(II) salen complex into a nanosilica matrix and characterized by TGA, XRD, atomic absorption spectroscopy and was successfully applied as catalyst for the oxidation of alcohols. Oxidation of a series of alcohols in acetonitrile over immobilized Mn(II) salen complex using tetrabutylammonium peroxymonosulfate (TBAO) as oxidant were resulted to the corresponding carbonyl compounds selectively in moderate to high yields. It is noteworthy that the aldehydes do not undergo further oxdation to carboxylic acids. The yields of aromatic alcohols are higher than those of alcohols with aliphatic groups. The catalyst has been reused several times, without observable loss of its activity and selectivity.

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[1] Y. Kohmura, T. Katsuki, Tetrahedron Lett., 2001, 42, 3339-3342.

[2] W.H. Sun, W. Wang, C.G. Xia, J.W. Li, P.Q. Zhao, Angew. Chem. Int. Ed., 2003, 42, 1042-1044.

[3] W. Sun, E. Herdtweck, F.E.  Kuhn, New J. Chem., 2005, 29, 1577-1580.

[4] E.M. McGarrigle, D.M. Murphy, D.G. Gilheany, Tetrahedron: Asymmetry., 2004, 15, 1343-1344.

[5] J.A. Gladysz, Chem. Rev., 2002, 102, 3215-3892.

[6] J.A. Gladysz, Pure Appl. Chem., 2001, 73, 1319-1324.

[7] D.E. De Vos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev., 2002, 102, 3615-3640.

[8] C.E. Song, S. Lee, Chem. Rev,. 2002, 102, 3495-3524.

[9] Q.H. Fan, Y.M. Li, A.S.C. Chan, Chem. Rev., 2002, 102, 3385-3466.

[10] R. Ferreira, M. Silva, C. Freire, B. de Castro, J.L. Figueiredo, Microporous Mesoporous Mater., 2000, 38, 391-401.

[11] R. Ferreira, C. Freire, B. de Castro, A.P. Carvalho, J. Pires, M. Brotas de Carvalho, Eur. J. Inorg. Chem., 2002, 11, 3032-3038.

[12] V. Ramaswamy, M. Sivarama Kirshnan, A.V. Ramaswamy, J. Mol. Catal. A: Chem., 2002, 181, 81-89.

[13] A.H. Lu, E.L. Salabas, F. Schu, Angew. Chem. Int. Ed., 2007, 46, 1222-1244.

[14] Y. Gao, C.S. Kumar, Wiley–VCH, Winheim., 2005, 1, 72-98.

[15] N. Matzaki, A. Sakamoto, N. Nagahashi, M. Soejima, Y.X. Li, T. Imamura, N. Kojima, H. Ohishi, K.I. Sakaquchi, C. Iwata, T. Tanaka J. Org .Chem., 2000, 65, 3284-3291.

[16] J. Fuhrhop, G. Penzlin, VCH: Weinheim 1994, 1-432.      

[17] A. Allahresani, M. A. Nasseri , RSC Adv., 2014, 4, 60702-60710.

[18] A. Mohammadinezhad, M.A. Nasseri, M. Salimi, RSC Adv., 2014, 4, 39870-39874.

[19] S. Velusamy, T. Punniyamurthy, Org. Lett., 2004, 6, 217-219.

[20] W.-H. Kim, I. S. Park, J. Park, Org. Lett., 2006, 8, 2543-2545.

[21] D. R. Jensen, M. J. Schultz, J. A. Mueller, M. S. Sigman, Angew. Chem. Int. Ed., 2003, 42, 3810-3813.

[22] I. A. Ansari, R. Gree, Org. Lett., 2002, 4, 1507-1509.

[23] G. An, M. Lim, K.-S. Chun, H. Rhee, Synlett, 2007, 95-98.