Abstract
A new silica based inorganic–organic hybrid zinc catalyst was synthesized and its catalytic activity was investigated for transesterification of β-ketoesters. Polymer supported catalyst was characterized by various techniques such as surface area (BET), elemental and thermogravimetric analyses, FTIR, 13C CPMAS spectral studies and atomic absorption spectroscopy (AAS). The reaction proceeded smoothly in the presence of 0.04 mmol of catalyst in toluene at refluxing conditions. The catalyst revealed higher catalytic activity compared to homogeneous catalyst and was reused without appreciable loss in catalytic activity.
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P.M. Price, J.H. Clark, D.J. Macquarrie, J. Chem. Soc., Dalton Trans., 101 (2000)
Q.H. Fan, Y.M. Li, A.S.C. Chan, Chem. Rev. 102, 3385 (2002)
N.E. Leadbeater, M. Marco, Chem. Rev. 102, 3217 (2002)
D. Brunel, N. Belloq, P. Sutra, A. Cauvel, M. Laspéras, P. Moreau, F. Di Renzo, A. Galarneau, F. Fajula, Coord. Chem. Rev. 178–180, 1085 (1998)
M.H. Valkenberg, W.F. Hölderich, Catal. Rev. 44, 321 (2002)
D.E. De Vos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev. 102, 3615 (2002)
B.M.L. Dioos, I.F.J. Vankelecom, P.A. Jacobs, Adv. Synth. Catal. 348, 1413 (2006)
A. Corma, H. Garcia, Adv. Synth. Catal. 348, 1391 (2006)
Z.L. Lu, E. Lindner, H.A. Mayer, Chem. Rev. 102, 3543 (2002)
A.P. Wight, M.E. Davis, Chem. Rev. 102, 3589 (2002)
R.K. Sharma, C. Sharma, J. Macromol. Sci. Pure Appl. Chem. Part A 48, 155 (2011)
R.K. Sharma, C. Sharma, Tetrahedron Lett. 51, 4415 (2010)
R.K. Sharma, D. Rawat, P. Pant, J. Macromol. Sci. Pure Appl. Chem. Part A 45, 394 (2008)
R.K. Sharma, D. Rawat, J. Inorg. Organomet. Polym. 20, 698 (2010)
R.K. Sharma, C. Sharma, J. Mol. Catal. A: Chem. 332, 53 (2010)
R.K. Sharma, C. Sharma, Catal. Commun. 12, 327 (2011)
J. Otera, Chem. Rev. 93, 1449 (1993)
U. Schuchardt, R. Sercheli, R.M. Vargas, J. Braz. Chem. Soc. 9, 199 (1998)
H. Hagiwara, A. Koseki, K. Isobe, K. Shimizu, T. Hoshi, T. Susuki, Synlett, 2188 (2004)
F.C. Da Silva, V.F. Ferreira, R.S. Rianelli, W.C. Perreira, Tetrahedron Lett. 43, 1165 (2002)
S. Benetti, R. Romagnoli, C. De Risi, G. Spalluto, V. Zanirato, Chem. Rev. 9, 1065 (1995)
C.E. Rehberg, C.H. Fischer, J. Am. Chem. Soc. 66, 1203 (1944)
S.P. Chavan, P.K. Zubaidha, N.R. Ayyangar, Tetrahedron Lett. 33, 4589 (1992)
D.F. Taber, J.C. Amedio Jr., Y.K. Patel, J. Org. Chem. 50, 3618 (1985)
D. Seebach, A. Thaler, D. Blaser, S.Y. Ko, Helv. Chim. Acta 74, 1102 (1991)
C. Blandy, J.L. Pellegatta, P. Cassoux, Catal. Lett. 43, 139 (1997)
L. Osipow, F.D. Snell, A. Finchler, J. Am. Oil Chem. Soc. 34, 185 (1957)
E. Santaniello, P. Ferraboschi, P. Grisenti, Enzyme Microb. Technol. 15, 367 (1993)
J. Otera, N. Dan-Oh, J. Nozaki, J. Org. Chem. 56, 5307 (1991)
B.C. Ranu, P. Dutta, A. Sarkar, J. Org. Chem. 63, 6027 (1998)
K. Pradeep, R.K. Pandey, Synlett, 251 (2000)
B.M. Reddy, V.R. Reddy, B. Manohar, Synth. Commun. 29, 1235 (1999)
B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, Synlett, 1338 (2001)
B.P. Bandgar. J. Chem. Res. (S), 16 (2001)
G. Shapiro, M. Marzi, J. Org. Chem. 62, 7096 (1997)
S.P. Chavan, R. Anand, K. Pasupathy, B.S. Rao, Green Chem., 320 (2001)
B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, Chem. Lett. 9, 894 (2001)
M.I. de Sairre, E.S. Bronze-Uhle, P.M. Donate, Tetrahedron Lett. 46, 2705 (2005)
P. Goswami, S.K. Bharadwaj, Catal. Lett. 124, 100 (2008)
Y.V.S. Rao, D.E. De Vos, P.A. Jacobs, Angew. Chem. Int. Ed. Engl. 36, 2661 (1997)
R.K. Sharma, S. Mittal, M. Koel, Crit. Rev. Anal. Chem. 3, 183 (2003)
J.S. Yadav, B.V.S. Reddy, A.D. Krishna, C.S. Reddy, A.V. Narsaiah, J. Mol. Catal. A: Chem. 261, 93 (2007)
B.S. Balaji, B.M. Chanda, Tetrahedron 54, 13237 (1998)
D.E. Ponde, V.H. Deshpande, V.J. Bulbule, A. Sudalai, A.S. Gajare, J. Org. Chem. 63, 1058 (1998)
W. Kamel, A.C. Cope, J. Am. Chem. Soc. 65, 1992 (1943)
D.S. Campbell, C.W. Lawrie, J. Chem. Soc. Chem. Commun., 355 (1971)
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Authors gratefully acknowledge IISc Bangalore for carrying out solid state NMR analyses.
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Sharma, R.K., Rawat, D. An Efficient and Recyclable Silica Based Inorganic–Organic Hybrid Zinc Catalyst for Transesterification of β-Ketoesters. J Inorg Organomet Polym 21, 619–626 (2011). https://doi.org/10.1007/s10904-011-9525-3
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DOI: https://doi.org/10.1007/s10904-011-9525-3