Mn(II) salen complex immobilized on nano silicagel as a recyclable heterogeneous catalyst for oxidation of alcohols to their corresponding carbonyl compounds

Nasseri, Mohammad Ali; Zakerinasab, Batol; Kamayestani, Sayyde

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.

Graphical Abstract

Keywords

Main Subjects

Nanochemistry

References

[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.

Iranian chemical communication

Mn(II) salen complex immobilized on nano silicagel as a recyclable heterogeneous catalyst for oxidation of alcohols to their corresponding carbonyl compounds

References

References

Volume 4, Issue 3, pp. 236-358, Serial No. 12
July 2016
Pages 283-294

Mn(II) salen complex immobilized on nano silicagel as a recyclable heterogeneous catalyst for oxidation of alcohols to their corresponding carbonyl compounds

References

References

Volume 4, Issue 3, pp. 236-358, Serial No. 12July 2016Pages 283-294

Volume 4, Issue 3, pp. 236-358, Serial No. 12
July 2016
Pages 283-294