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Application of Copper(II) Schiff Base Complex Grafted in the Silica Network as Efficient Nanocatalyst in Oxidation of Alcohols
Corresponding Author(s) : Hossein Eshtiagh-Hosseini
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
Bis[S-allyl-b-N-(benzylidene)dithiocarbazato]copper(II) complex was grafted into SiO2 matrix. Heterogenized catalyst was characterized by FT-IR, SEM, EDX TEM, N2 absorption and atomic absorption spectroscopy (AAS) and its catalytic performance in the oxidation of alcohols was investigated. The experimental results showed that the prepared heterogeneous nanocatalyst is an efficient and selective catalyst for examined oxidation reaction. Thus, secondary alcohols were oxidized to ketones and primery alcohols converted to aldehydes by hydrogen peroxide in the presence of newly nanocatalyst in mild conditions.
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- E.N. Jacobsen, W. Zhang and M.L. Guler, J. Am. Chem. Soc., 113, 6703 (1991).
- E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker and L. Deng, J. Am. Chem. Soc, 113, 7063 (1991).
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- S.E. Schaus, J. Branalt and E.N. Jacobsen, J. Org. Chem., 63, 403 (1998).
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- A.M. Daly, C.T. Dalton, M.F. Renehan and D.G. Gilheany, Tetrahedron Lett., 40, 3617 (1999).
- M. Tokunaga, J.F. Larrow, F. Kakiuchi and E.N. Jacobsen, Science, 277, 936 (1997).
- J.P. Collman, V.J. Lee, C.J. Kellen-Yuen, X. Zhang, J.A. Ibers and J.I. Brauman, J. Am. Chem. Soc., 117, 692 (1995).
- K.J. Ballus, A.K. Khanmamedova, K.M. Dixon and F. Bedioui, Appl. Catal. A, 143, 159 (1996).
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- Z. Li, K.R. Conser and E.N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993).
- C.R. Jacob, S.P. Varkey and P. Ratnasamy, Micropor. Mesopor. Mater., 22, 465 (1998).
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- H. Zhang, S. Xiang and C. Li, Chem. Commun., 1209 (2005).
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- P. Karandikar, K.C. Dhanya, S. Deshpande, A.J. Chanwadkar, S. Sivasanker and A. Agashe, Catal. Commun., 5, 69 (2004).
- R.A. Sheldon and J.K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York (1981).
- M. Yazdanbakhsh, M.M. Heravi, R. Takjoo and W. Frank, Z. Anorg. Allg. Chem., 634, 972 (2008).
- F. Bedioui, Coord. Chem. Rev., 144, 39 (1995)
References
E.N. Jacobsen, W. Zhang and M.L. Guler, J. Am. Chem. Soc., 113, 6703 (1991).
E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker and L. Deng, J. Am. Chem. Soc, 113, 7063 (1991).
W. Zhang, J.L. Loebach, S.R. Wilson and E.N. Jacobsen, J. Am. Chem. Soc., 112, 2801 (1990).
S.E. Schaus, J. Branalt and E.N. Jacobsen, J. Org. Chem., 63, 403 (1998).
J. Lopez and S. Liang, Tetrahedron Lett., 39, 4199 (1998).
A.M. Daly, C.T. Dalton, M.F. Renehan and D.G. Gilheany, Tetrahedron Lett., 40, 3617 (1999).
M. Tokunaga, J.F. Larrow, F. Kakiuchi and E.N. Jacobsen, Science, 277, 936 (1997).
J.P. Collman, V.J. Lee, C.J. Kellen-Yuen, X. Zhang, J.A. Ibers and J.I. Brauman, J. Am. Chem. Soc., 117, 692 (1995).
K.J. Ballus, A.K. Khanmamedova, K.M. Dixon and F. Bedioui, Appl. Catal. A, 143, 159 (1996).
C. Heinrichs and W.F. Holderich, Catal. Lett. Catal. Lett., 58, 75 (1999).
G.J. Kim and J.H. Shin, Tetrahedron Lett., 40, 6827 (1999).
D.W. Park, S.D. Choi, S.J. Choi, C.Y. Lee and G.J. Kim, Catal. Lett., 78, 145 (2002).
C. Mossner and C. Bolm, in eds.: M. Beller and C. Bolm, Transition Metals for Organic Synthesis, Wiley-WCH Verlag, Weinheim, edn 2, pp. 389–402 (2004).
Z. Li, K.R. Conser and E.N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993).
C.R. Jacob, S.P. Varkey and P. Ratnasamy, Micropor. Mesopor. Mater., 22, 465 (1998).
P. Klement, F. Stock, H. Elias, H. Paulus, P. Pelikán, M. Valko, M. Mazúr, Polyhedron, 18, 3617 (1999).
Z. Li, Z. Zheng, B. Wan and H. Chen, J. Mol. Catal. A, 165, 67 (2001).
Y.N. Belokon, J. Fuentes, M. North and J.W. Steed, Tetrahedron, 60, 3191 (2004).
C. Bianchini and P. Barbaro, Top. Catal., 19, 17 (2002).
C.E. Song and S.G. Lee, Chem. Rev., 102, 3495 (2002).
A.R. Silva, M.M.A. Freitas, C. Freire, B. de Castro and J.L. Figueiredo, Langmuir, 18, 8017 (2002).
P. Memorn and C. Hutchings, J. Soc. Rev., 33, 108 (2004).
C. Li, Catal. Rev. Sci. Eng., 46, 419 (2004).
V. Ayala, A. Corma, M. Iglesias and F. Sánchez, J. Mol. Catal., 221, 201 (2004).
A. Sakthivel, J. Zhao, G. Raudaschl-Sieber, A.S.T. Chiang and F.E. Kühn, Appl. Catal. A, 281, 267 (2005).
H. Zhang, S. Xiang and C. Li, Chem. Commun., 1209 (2005).
A. Sakthivel, J. Zhao and F.E. Kühn, Catal. Lett., 102, 115 (2005).
F.E. Murphy, L. Schmid, T. Buergi, M. Maciejewski, A. Baiker, D. Guenther and M. Schneider, Chem. Mater., 13, 1296 (2001).
P. Karandikar, K.C. Dhanya, S. Deshpande, A.J. Chanwadkar, S. Sivasanker and A. Agashe, Catal. Commun., 5, 69 (2004).
R.A. Sheldon and J.K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York (1981).
M. Yazdanbakhsh, M.M. Heravi, R. Takjoo and W. Frank, Z. Anorg. Allg. Chem., 634, 972 (2008).
F. Bedioui, Coord. Chem. Rev., 144, 39 (1995)