Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access December 1, 2007

Ionic liquid-functionalized SBA-15 mesoporous material: efficient heterogeneous catalyst in versatile organic reactions

Li-Wen Xu, Ming-Song Yang, Jian-Xiong Jiang, Hua-Yu Qiu and Guo-Qiao Lai
From the journal Open Chemistry


Ionic liquid-functionalized mesoporous materials exhibited high catalytic activity in versatile organic reactions, such as cycloaddition of carbon dioxide (CO2) with epoxide, aza-Michael addition of amines to α, β-unsaturated carbonyl compounds, and the Biginelli reaction of aldehyde, ethyl acetoacetate and urea. Recycling of the catalyst in these reactions could be carried out and the catalyst used at least five times without significant loss in activity.

[1] J. Dupont, R.F. de Souza and P.A.Z. Suarez: “Ionic Liquid (Molten Salt) Phase Organometallic Catalysis”, Chem. Rev., Vol. 102, (2002), pp. 3667–3692. in Google Scholar

[2] L.W. Xu, Y. Gao, J.J. Yin, L. Li and C.G. Xia: “Efficient and mild benzoin condensation reaction catalyzed by simple 1-N-alkyl-3-methylimidazolium salts”, Tetrahedron Lett., Vol. 46, (2005), pp. 5317–5320. in Google Scholar

[3] A.R. Katritzky, S. Singh, K. Kirichenko, J.D. Holbrey, M. Smiglak, W.M. Reichert and R.D. Rogers: “1-Butyl-3-methylimidazolium 3,5-dinitro-1,2,4-triazolate: a novel ionic liquid containing a rigid, planar energetic anion”, Chem. Commun., (2005), pp. 868–870. Search in Google Scholar

[4] K. Fukumoto, M. Yoshizawa and H. Ohno: “Room Temperature Ionic Liquids from 20 Natural Amino Acids”, J. Am. Chem. Soc., Vol. 127, (2005), pp. 2398–2399. in Google Scholar

[5] E.B. Carter, S.L. Culver, P.A. Fox, R.D. Goode, I. Ntai, M.D. Tickell, R.K. Traylor, N.W. Hoffman and J.H. Davis: “Sweet success: ionic liquids derived from nonnutritive sweeteners”, Chem. Commun., (2004), pp. 630–631. Search in Google Scholar

[6] G. Imperato, E. Eibler, J. Niedermaier and B. König: “Low-melting sugar-urea-salt mixtures as solvents for Diels-Alder reactions”, Chem. Commun., (2005), pp. 1170–1172. Search in Google Scholar

[7] C.J. Adams, M.J. Earle and K.R. Seddon: “Stereoselective hydrogenation reactions in chloroaluminate(III) ionic liquids: a new method for the reduction of aromatic compounds”, J. Chem. Soc. Chem. Commun., (1999), pp. 1043–1044. Search in Google Scholar

[8] J. Howarth: “Oxidation of aromatic aldehydes in the ionic liquid [bmim]PF6”, Tetrahedron Lett., Vol. 41, (2000), pp. 6627–6629. in Google Scholar

[9] G.S. Owens and M.M. Abu-Omar: “Methyltrioxorhenium-catalyzed epoxidations in ionic liquids”, J. Chem. Soc. Chem. Commun., (2000), pp. 1165–1166. Search in Google Scholar

[10] C.C. Brasse, U. Englert, A. Salzer, H. Waffenschmidt and P. Wasserscheid: “Ionic Phosphine Ligands with Cobaltocenium Backbone: Novel Ligands for the Highly Selective, Biphasic, Rhodium-Catalyzed Hydroformylation of 1-Octene in Ionic Liquids”, Organometallics, Vol. 19, (2000), pp. 3818–3823. in Google Scholar

[11] C.J. Adams, M.J. Earle, G. Roberts and K.R. Seddon: “Friedel-Crafts reactions in room temperature ionic liquids”, J. Chem. Soc., Chem. Commun., (1998), pp. 2097–2098. Search in Google Scholar

[12] C.E. Song, W.H. Shim, E.J. Roh and J.H. Choi: “Scandium(III) triflate immobilised in ionic liquids: a novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes”, J. Chem. Soc. Chem. Commun., (2000), pp. 1695–1696. Search in Google Scholar

[13] W. Chen, L. Xu, C. Chatterton and J. Xiao: “Palladium catalysed allylation reactions in ionic liquids”, J. Chem. Soc. Chem. Commun., (1999), pp. 1247–1248. Search in Google Scholar

[14] M.J. Earle, P.B. McCormac and K.R. Seddon: “Diels-Alder reactions in ionic liquids. A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures”, Green Chem., Vol. 1, (1999), pp. 23–25. in Google Scholar

[15] A.J. Carmichael, M.J. Earle, J.D. Holbrey, P.B. McCormac and K.R. Seddon: “The Heck Reaction in Ionic Liquids: A Multiphasic Catalyst System”, Org. Lett., Vol. 1, (1999), pp. 997–1000. in Google Scholar

[16] C.J. Mathews, P.J. Smith and T. Welton: “Palladium catalysed Suzuki cross-coupling reactions in ambient temperature ionic liquids”, J. Chem. Soc. Chem. Commun., (2000), pp. 1249–1250. Search in Google Scholar

[17] C. de Bellefon, E. Pollet and P. Grenouillet: “Molten salts (ionic liquids) to improve the activity, selectivity and stability of the palladium catalysed Trost-Tsuji C-C coupling in biphasic media”, J. Mol. Catal. A-Chem., Vol. 145, (1999), pp. 121–126. in Google Scholar

[18] A. Corma and H. Garcia: “Silica-Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis”, Adv. Synth. Catal., Vol. 348, (2006), pp. 1391–1412. in Google Scholar

[19] K. Qiao, H. Hagiwara and C. Yokoyama: “Acidic ionic liquid modified silica gel as novel solid catalysts for esterification and nitration reactions”, J. Mol. Catal. A-Chem., Vol. 246, (2006), pp. 65–69. in Google Scholar

[20] Y. Liu, J. Peng, S. Zhai, J. Li, J, Mao, M. Li, H. Qiu and G. Lai: “Synthesis of Ionic Liquid Functionalized SBA-15 Mesoporous Materials as Heterogeneous Catalyst toward Knoevenagel Condensation under Solvent-Free Conditions”, Eur. J. Inorg. Chem., (2006), pp. 2947–2949. Search in Google Scholar

[21] M.E. Jung: “Stabilized nucleophiles with electron deficient alkenes and alkynes”, In: B.M. Trost, I. Fleming, (Eds.), Comprehensive Organic Synthesis, Pergamon: Oxford, 1991; Vol. 4, p. 30. Search in Google Scholar

[22] L.W. Xu, C.G. Xia, H. Wu, L. Yang, W. Zhou and Y. Zhang: “Progress in Aza-Michael reaction”, Chin. J. Org. Chem., Vol. 25, (2005), pp. 167–175. in Google Scholar

[23] B. Basu, P. Das and I. Hossain: “Synthesis of β-Amino Esters via Aza-Michael Addition of Amines to Alkenes Promoted on Silica: A Useful and Recyclable Surface”, Synlett, (2004), pp. 2630–2632. Search in Google Scholar

[24] D.H. Dibson: “The Organometallic Chemistry of Carbon Dioxide”, Chem. Rev., Vol. 96, (1996), pp. 2063–2096. in Google Scholar PubMed

[25] V. Amarnath and A.D. Broom: “Chemical synthesis of oligonucleotides”, Chem. Rev., Vol. 77, (1977), pp. 183–217. in Google Scholar

[26] F.W. Li, C.G. Xia, L.W. Xu, C.G. Xia, W. Sun and G.X. Chen: “A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides”, Chem. Commun., (2003), pp. 2042–2043. Search in Google Scholar

[27] Z.D. Aron and L.E. Overman: “The tethered Biginelli condensation in natural product synthesis”, Chem. Commun., (2004), pp. 253–265. Search in Google Scholar

[28] L.W. Xu, Z.T. Wang, C.G. Xia, L. Li and P.Q. Zhao: “Improved protocol for the three-component Biginelli reactions and Bigimelli-like Mannich reactions of carbamates, aldehydes, and ketones”, Helv. Chim. Acta, Vol. 87, (2004), pp. 2608–2612. in Google Scholar

Published Online: 2007-12-1
Published in Print: 2007-12-1

© 2007 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Scroll Up Arrow