SO3H - Functionalized Acidic Ionic Liquid Catalysts in Organic Reactions
Abstract
This review concluded the utilization of SO3H-functionalized ionic liquids bearing imidazolium, pyridinium, phosphonium or ammonium cations and various acids couteranions in numerous organic reactions as efficient solvents, reagents and catalysts. Some of the versatile organic reactions are described in this review, including esterification, Mannich reaction, Friedel-Crafts reaction, nitration, Beckmann rearrangement, Friedlander reaction, Michael addition, multicomponent reaction and Fisher indole synthesis. Advantages of these SO3H-functionalized ionic liquids can promote the reactions efficiently, providing the products in high yields and can be reused in several times without significant loss of catalytic activity. Keywords : acidic ionic liquid, organic reaction, Brönsted acidic catalystReferences
Akbari, J., Heydari, A., Kalhor, H. R. & Kohan, S. A. (2010). Sulfonic acid functionalized ionic liquid in combinatorial approach, a recyclable and water tolerant-acidic catalyst for one-pot Friedlander quinoline synthesis. J. Comb. Chem., 12, 137-140.
Akiyama, T., Takaya, J., Kagoshima, H. (2002). Brönsted acid-catalyzed Mannich-type reactions in aqueous media. Adv. Synth. Catal., 344, 338-347.
Amarasekara, A. S. & Hasan, M. A. (2014). 1-(1-Alkylsulfonic)-3-methylimidazolium chloride Brönsted acidic ionic liquid catalyzed Skraup synthesis of quinolones under microwave heating. Tetrahedron Lett., 55, 3319-3321.
Amarasekara, A. S. (2016). Acidic ionic liquids. Chem. Rev., 116, 6133-6183.
Bagdi, A. K. & Hajra, A. (2014). Brönsted acidic ionic liquid catalyzed tandem reaction of 4-hydroxy-1-methyl-2-quinolone with chalcone: regioselective synthesis of pyrano[3,2-c]quinolin-2-ones. RSC. Adv., 4, 23287-23291.
Chang, T., He, L., Bian, L., Han, H., Yuan, M. & Gao, X. (2014). Brönsted acid-surfactant-combined catalyst for the Mannich reaction in water. RSC Adv., 4, 727-731.
Cole, A. C., Jensen, J. L., Ntai, I., Tran, K. L. T., Weaver, K. J., Forbes, D.C. & Davis, J. H. Jr. (2002). Novel Brönsted acidic ionic liquids and their use as dual solvent-catalysts. J. Am. Chem. Soc.,124, 5962-5963.
Duan, Z., Gu, Y., Zhang, J., Zhu, L. & Deng, Y. (2006). Protic pyridinium ionic liquids: synthesis, activity determination and their performances for acid catalysis. J. Mol. Catal. A: Chem., 250, 163-168.
Fang, D., Fei, Z. & Liu, Z. (2009). Functionalized ionic liquid as the recyclable catalyst for Mannich-type reaction in aqueous media. Catal. Commun., 10, 1267-1270.
Fang, D., Luo, J., Zhou, X. -L. & Liu, Z .-L. (2007). Mannich reaction in water using acidic ionic liquid as recoverable and reusable catalyst. Catal. Lett., 116, 76-80.
Fang, D., Shi, Q. -R., Cheng, J., Gong, K. & Liu, Z. -L. (2008). Regioselective mononitration of aromatic compounds using Brönsted acidic ionic liquids as recoverable catalysts. Appl. Catal. A: Gen., 345, 158-163.
Fang, D., Zhou, X. -L., Ye, Z. -W. & Liu, Z. -L. (2006). Brönsted acidic ionic liquid and their use as dual solvent-catalysts for Fischer esterification. Ind. Eng. Chem. Res., 45, 7982-7984.
Fraga-Dubreuil, J., Bourahla, K., Rahmouni, M., Bazureau, J. P. & Hamelin, J. (2002). Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media. Catal. Commun., 3, 185-190.
Gu, Y., Shi, F. & Deng, Y. (2004). Esterification of aliphatic acids with olefin promoted by Brönsted acidic ionic liquids. J. Mol. Catal. A: Chem., 212, 71-75.
Hajipour, A. R., Ghayeb, Y., Sheikhan, N. & Ruoho, A. E. (2009). Brönsted acidic ionic liquid as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl 2-naphthols under solvent-free conditions. Tetrahedron Lett., 50, 5649-5651.
Han, F., Yang, L., Li, Z. & Xia, C. (2012). Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to -unsaturated ketones. Org. Biomol. Chem., 10, 346-354.
He, L., Qin, S., Chang, T., Sun, Y. & Gao, X. (2013). Biodiesel synthesis from the esterification of three fatty acids and alcohol catalyzed by long-chain Bronsted acid ionic liquid. Catal. Sci. Technol., 3, 1102-1107.
Kitaoka, S., Nobuoka, K. & Ishikawa, Y. (2004). The first utilization of acidic ionic liquid for preparation of tetraarylporphyrins. Chem. Commun., 1902-1903.
Li, B. L., Xu, D. –Q., Zhong, A. G. (2012). Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fisher indole synthesis in water under microwave irradiation. J. Fluorine Chem., 144, 45-50.
Li, J., Peng, Y. & Song, G. (2005). Mannich reaction catalyzed by carboxyl-functionalized ionic liquid in aqueous media. Catal. Lett., 102, 159-162.
Limura, S., Nobutou, D., Manable, K., Kobayashi, S. (2003). Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst. Chem. Commun., 1644-1645.
Liu, X., Xiao, L., Wu, H., Li, Z., Chen, J. & Xia, C. (2009). Novel acidic ionic liquids mediated zinc chloride: highly effective catalysts for the Beckmann rearrangement. Catal. Commun., 10, 424-427.
Qiao, K., Hagiwara, H. & Yokoyama, C. (2006). Acidic ionic liquid modified silica gel as novel solid catalysts for esterification and nitration reactions. J. Mol. Catal. A: Chem., 246, 65-69.
Sahoo, S., Joseph, T. & Halligudi, S. B. (2006). Mannich reaction in Brönsted acidic ionic liquid: A facile synthesis of -amino carbonyl compounds. J. Mol. Catal. A: Chem., 244, 179-182.
Senapak, W., Saeeng, R., Jaratjaroonphong, J., Kasemsuk, T. & Sirion, U. (2016). Green synthesis of dipyrromethanes in aqueous media catalyzed by SO3H-functionalized ionic liquid. Org. Biomol. Chem., 14, 1302-1310.
Taheri, A., Lai, B., Cheng, C. & Gu, Y. (2015). Brönsted acid ionic liquid-catalyzed reductive Friedel-Crafts alkylation of indoles and cyclic ketones without an external reductant. Green Chem., 812-816.
Taheri, A., Liu, C., Lai, B., Cheng, C., Pan, X. & Gu, Y. (2014). Brönsted acidic ionic liquid catalyzed facile synthesis of 3-vinylindoles through direct C3 alkenylation of indoles with simple ketones. Green Chem., 16, 3715-3719.
Xing, H., Wang, T., Zhou, Z. & Dai, Y. (2005). Novel Brönsted-acidic ionic liquids for esterifications. Ind. Eng. Chem. Res., 44, 4147-4150.
Xu, D. -Q., Wu, J., Luo, S. -P., Zhang, J. -X., Wu, J. -Y., Du, X. -H. & Xu, Z. -Y. (2009). Fisher indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water. Green Chem., 11, 1239-1246.
Xu, Z., Wan, H., Miao, J., Han, M., Yang, C. & Guan, G. (2010). Reusable and efficient polystyrene-supported acidic ionic liquid catalyst for esterification. J. Mol. Catal. A: Chem., 322, 152-157.
Yue, C. B., Yi, T.F., Zhu, C. B. & Liu, G. (2009). Mannich reaction catalyzed by a novel catalyst under solvent-free conditions. J. Indust. Eng. Chem., 15, 653-656.
Zare, A., Abi, F., Moosavi-Zare, A. R., Beyzavi, M.H. & Zolfigol, M. A. (2013). Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines. J. Mol. Liq., 178, 113-121.
Zhao, G., Jiang, T., Gao, H., Han, B., Huang, J. & Sun, D. (2004). Mannich reaction using acidic ionic liquids as catalysts and solvents. Green Chem., 6, 75-77.
Zolfigol, M. A., Khazaei, A., Moosavi-Zare, A. R., Zare, A., Kruger, H. G., Asgari, Z., Khakyzadeh, V. & Kazem[Rostami, M. (2012). Design of ionic liquid 3-methyl-1-sulfonic acid imidazoilum nitrate as reagent for the nitration of aromatic compounds by in Situ generation of NO2 in acidic media. J. Org. Chem., 77, 3640-3645.
Akiyama, T., Takaya, J., Kagoshima, H. (2002). Brönsted acid-catalyzed Mannich-type reactions in aqueous media. Adv. Synth. Catal., 344, 338-347.
Amarasekara, A. S. & Hasan, M. A. (2014). 1-(1-Alkylsulfonic)-3-methylimidazolium chloride Brönsted acidic ionic liquid catalyzed Skraup synthesis of quinolones under microwave heating. Tetrahedron Lett., 55, 3319-3321.
Amarasekara, A. S. (2016). Acidic ionic liquids. Chem. Rev., 116, 6133-6183.
Bagdi, A. K. & Hajra, A. (2014). Brönsted acidic ionic liquid catalyzed tandem reaction of 4-hydroxy-1-methyl-2-quinolone with chalcone: regioselective synthesis of pyrano[3,2-c]quinolin-2-ones. RSC. Adv., 4, 23287-23291.
Chang, T., He, L., Bian, L., Han, H., Yuan, M. & Gao, X. (2014). Brönsted acid-surfactant-combined catalyst for the Mannich reaction in water. RSC Adv., 4, 727-731.
Cole, A. C., Jensen, J. L., Ntai, I., Tran, K. L. T., Weaver, K. J., Forbes, D.C. & Davis, J. H. Jr. (2002). Novel Brönsted acidic ionic liquids and their use as dual solvent-catalysts. J. Am. Chem. Soc.,124, 5962-5963.
Duan, Z., Gu, Y., Zhang, J., Zhu, L. & Deng, Y. (2006). Protic pyridinium ionic liquids: synthesis, activity determination and their performances for acid catalysis. J. Mol. Catal. A: Chem., 250, 163-168.
Fang, D., Fei, Z. & Liu, Z. (2009). Functionalized ionic liquid as the recyclable catalyst for Mannich-type reaction in aqueous media. Catal. Commun., 10, 1267-1270.
Fang, D., Luo, J., Zhou, X. -L. & Liu, Z .-L. (2007). Mannich reaction in water using acidic ionic liquid as recoverable and reusable catalyst. Catal. Lett., 116, 76-80.
Fang, D., Shi, Q. -R., Cheng, J., Gong, K. & Liu, Z. -L. (2008). Regioselective mononitration of aromatic compounds using Brönsted acidic ionic liquids as recoverable catalysts. Appl. Catal. A: Gen., 345, 158-163.
Fang, D., Zhou, X. -L., Ye, Z. -W. & Liu, Z. -L. (2006). Brönsted acidic ionic liquid and their use as dual solvent-catalysts for Fischer esterification. Ind. Eng. Chem. Res., 45, 7982-7984.
Fraga-Dubreuil, J., Bourahla, K., Rahmouni, M., Bazureau, J. P. & Hamelin, J. (2002). Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media. Catal. Commun., 3, 185-190.
Gu, Y., Shi, F. & Deng, Y. (2004). Esterification of aliphatic acids with olefin promoted by Brönsted acidic ionic liquids. J. Mol. Catal. A: Chem., 212, 71-75.
Hajipour, A. R., Ghayeb, Y., Sheikhan, N. & Ruoho, A. E. (2009). Brönsted acidic ionic liquid as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl 2-naphthols under solvent-free conditions. Tetrahedron Lett., 50, 5649-5651.
Han, F., Yang, L., Li, Z. & Xia, C. (2012). Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to -unsaturated ketones. Org. Biomol. Chem., 10, 346-354.
He, L., Qin, S., Chang, T., Sun, Y. & Gao, X. (2013). Biodiesel synthesis from the esterification of three fatty acids and alcohol catalyzed by long-chain Bronsted acid ionic liquid. Catal. Sci. Technol., 3, 1102-1107.
Kitaoka, S., Nobuoka, K. & Ishikawa, Y. (2004). The first utilization of acidic ionic liquid for preparation of tetraarylporphyrins. Chem. Commun., 1902-1903.
Li, B. L., Xu, D. –Q., Zhong, A. G. (2012). Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fisher indole synthesis in water under microwave irradiation. J. Fluorine Chem., 144, 45-50.
Li, J., Peng, Y. & Song, G. (2005). Mannich reaction catalyzed by carboxyl-functionalized ionic liquid in aqueous media. Catal. Lett., 102, 159-162.
Limura, S., Nobutou, D., Manable, K., Kobayashi, S. (2003). Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst. Chem. Commun., 1644-1645.
Liu, X., Xiao, L., Wu, H., Li, Z., Chen, J. & Xia, C. (2009). Novel acidic ionic liquids mediated zinc chloride: highly effective catalysts for the Beckmann rearrangement. Catal. Commun., 10, 424-427.
Qiao, K., Hagiwara, H. & Yokoyama, C. (2006). Acidic ionic liquid modified silica gel as novel solid catalysts for esterification and nitration reactions. J. Mol. Catal. A: Chem., 246, 65-69.
Sahoo, S., Joseph, T. & Halligudi, S. B. (2006). Mannich reaction in Brönsted acidic ionic liquid: A facile synthesis of -amino carbonyl compounds. J. Mol. Catal. A: Chem., 244, 179-182.
Senapak, W., Saeeng, R., Jaratjaroonphong, J., Kasemsuk, T. & Sirion, U. (2016). Green synthesis of dipyrromethanes in aqueous media catalyzed by SO3H-functionalized ionic liquid. Org. Biomol. Chem., 14, 1302-1310.
Taheri, A., Lai, B., Cheng, C. & Gu, Y. (2015). Brönsted acid ionic liquid-catalyzed reductive Friedel-Crafts alkylation of indoles and cyclic ketones without an external reductant. Green Chem., 812-816.
Taheri, A., Liu, C., Lai, B., Cheng, C., Pan, X. & Gu, Y. (2014). Brönsted acidic ionic liquid catalyzed facile synthesis of 3-vinylindoles through direct C3 alkenylation of indoles with simple ketones. Green Chem., 16, 3715-3719.
Xing, H., Wang, T., Zhou, Z. & Dai, Y. (2005). Novel Brönsted-acidic ionic liquids for esterifications. Ind. Eng. Chem. Res., 44, 4147-4150.
Xu, D. -Q., Wu, J., Luo, S. -P., Zhang, J. -X., Wu, J. -Y., Du, X. -H. & Xu, Z. -Y. (2009). Fisher indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water. Green Chem., 11, 1239-1246.
Xu, Z., Wan, H., Miao, J., Han, M., Yang, C. & Guan, G. (2010). Reusable and efficient polystyrene-supported acidic ionic liquid catalyst for esterification. J. Mol. Catal. A: Chem., 322, 152-157.
Yue, C. B., Yi, T.F., Zhu, C. B. & Liu, G. (2009). Mannich reaction catalyzed by a novel catalyst under solvent-free conditions. J. Indust. Eng. Chem., 15, 653-656.
Zare, A., Abi, F., Moosavi-Zare, A. R., Beyzavi, M.H. & Zolfigol, M. A. (2013). Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines. J. Mol. Liq., 178, 113-121.
Zhao, G., Jiang, T., Gao, H., Han, B., Huang, J. & Sun, D. (2004). Mannich reaction using acidic ionic liquids as catalysts and solvents. Green Chem., 6, 75-77.
Zolfigol, M. A., Khazaei, A., Moosavi-Zare, A. R., Zare, A., Kruger, H. G., Asgari, Z., Khakyzadeh, V. & Kazem[Rostami, M. (2012). Design of ionic liquid 3-methyl-1-sulfonic acid imidazoilum nitrate as reagent for the nitration of aromatic compounds by in Situ generation of NO2 in acidic media. J. Org. Chem., 77, 3640-3645.
Downloads
Published
2016-08-11
Issue
Section
Scientific Article
