Sulfonated poly(4-vinylpyridine) heteropolyacid salts:A reusable green solid catalyst for Mannich reaction
English
Sulfonated poly(4-vinylpyridine) heteropolyacid salts:A reusable green solid catalyst for Mannich reaction
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Key words:
- Mannich reaction
- / Heteropolyacid
- / Poly(4-vinylpyridine)
- / Heterogeneous catalyst
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[1] M. Arend, B. Westermann, N. Risch, Modern variants of the Mannich reaction, Angew. Chem. Int. Ed. 37 (1998) 1044-1070.[1] M. Arend, B. Westermann, N. Risch, Modern variants of the Mannich reaction, Angew. Chem. Int. Ed. 37 (1998) 1044-1070.
-
[2] S. Kobayashi, H. Ishitani, Catalytic enantioselective addition to imines, Chem. Rev. 99 (1999) 1069-1094.[2] S. Kobayashi, H. Ishitani, Catalytic enantioselective addition to imines, Chem. Rev. 99 (1999) 1069-1094.
-
[3] R. Muller, H. Goesmann, H. Waldmann, N,N-Phthaloylamino acids as chiral auxiliaries in asymmetric Mannich-type reactions, Angew. Chem. Int. Ed. 38 (1999) 184-187.[3] R. Muller, H. Goesmann, H. Waldmann, N,N-Phthaloylamino acids as chiral auxiliaries in asymmetric Mannich-type reactions, Angew. Chem. Int. Ed. 38 (1999) 184-187.
-
[4] H. Bohme, M. Haake, in: E.C. Taylor (Ed.), Advances in Organic Chemistry, vol. 7, John Wiley and Sons, New York, 1976, p. 107.[4] H. Bohme, M. Haake, in: E.C. Taylor (Ed.), Advances in Organic Chemistry, vol. 7, John Wiley and Sons, New York, 1976, p. 107.
-
[5] M. Suginome, L. Uehlin, M. Murakami, Aminoboranes as "compatible" iminium ion generators in aminative C-C bond formations, J. Am. Chem. Soc. 126 (2004) 13196-13197.[5] M. Suginome, L. Uehlin, M. Murakami, Aminoboranes as "compatible" iminium ion generators in aminative C-C bond formations, J. Am. Chem. Soc. 126 (2004) 13196-13197.
-
[6] W. Notz, F. Tanaka, S.I. Watanabe, et al., The direct organocatalytic asymmetric Mannich reaction: unmodified aldehydes as nucleophiles, J. Org. Chem. 68 (2003) 9624-9634.[6] W. Notz, F. Tanaka, S.I. Watanabe, et al., The direct organocatalytic asymmetric Mannich reaction: unmodified aldehydes as nucleophiles, J. Org. Chem. 68 (2003) 9624-9634.
-
[7] B.M. Trost, L.R. Terrell, A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols, J. Am. Chem. Soc. 125 (2003) 338-339.[7] B.M. Trost, L.R. Terrell, A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols, J. Am. Chem. Soc. 125 (2003) 338-339.
-
[8] S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, Anti-selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing β-amino alcohols, J. Am. Chem. Soc. 125 (2003) 4712-4713.[8] S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, Anti-selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing β-amino alcohols, J. Am. Chem. Soc. 125 (2003) 4712-4713.
-
[9] K. Juhl, N. Gathergood, K.A. Jørgensen, Catalytic asymmetric direct Mannich reactions of carbonyl compounds with a-imino esters, Angew. Chem. Int. Ed. 40 (2001) 2995-2997.[9] K. Juhl, N. Gathergood, K.A. Jørgensen, Catalytic asymmetric direct Mannich reactions of carbonyl compounds with a-imino esters, Angew. Chem. Int. Ed. 40 (2001) 2995-2997.
-
[10] B. List, The direct catalytic asymmetric three-component Mannich reaction, J. Am. Chem. Soc. 122 (2000) 9336-9337.[10] B. List, The direct catalytic asymmetric three-component Mannich reaction, J. Am. Chem. Soc. 122 (2000) 9336-9337.
-
[11] B. List, P. Pojarliev, W.T. Biller, H.J. Martin, The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohol, J. Am. Chem. Soc. 124 (2002) 827-833.[11] B. List, P. Pojarliev, W.T. Biller, H.J. Martin, The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohol, J. Am. Chem. Soc. 124 (2002) 827-833.
-
[12] A. Cordova, W. Notz, G. Zhong, J.M. Betancort, C.F. Barbas, A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids, J. Am. Chem. Soc. 124 (2002) 1842-1943.[12] A. Cordova, W. Notz, G. Zhong, J.M. Betancort, C.F. Barbas, A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids, J. Am. Chem. Soc. 124 (2002) 1842-1943.
-
[13] S. Kobayashi, T. Hamada, K. Manabe, The catalytic asymmetric Mannich-type reactions in aqueous media, J. Am. Chem. Soc. 124 (2002) 5640-5641.[13] S. Kobayashi, T. Hamada, K. Manabe, The catalytic asymmetric Mannich-type reactions in aqueous media, J. Am. Chem. Soc. 124 (2002) 5640-5641.
-
[14] Y. Hayashi, W. Tsuboi, I. Ashimine, et al., The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes, Angew. Chem. Int. Ed. 42 (2003) 3677-3680.[14] Y. Hayashi, W. Tsuboi, I. Ashimine, et al., The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes, Angew. Chem. Int. Ed. 42 (2003) 3677-3680.
-
[15] A.G. Wenzel, E.N. Jacobsen, Asymmetric catalytic mannich reactions catalyzed by urea derivatives: enantioselective synthesis of b-aryl-β-amino acids, J. Am. Chem. Soc. 124 (2002) 12964-12965.[15] A.G. Wenzel, E.N. Jacobsen, Asymmetric catalytic mannich reactions catalyzed by urea derivatives: enantioselective synthesis of b-aryl-β-amino acids, J. Am. Chem. Soc. 124 (2002) 12964-12965.
-
[16] S. Sahoo, T. Joseph, S.B. Halligudi, Mannich reaction in Bro¨nsted acidic ionic liquid: a facile synthesis of β-amino carbonyl compounds, J. Mol. Catal. A: Chem. 244 (2006) 179-182.[16] S. Sahoo, T. Joseph, S.B. Halligudi, Mannich reaction in Bro¨nsted acidic ionic liquid: a facile synthesis of β-amino carbonyl compounds, J. Mol. Catal. A: Chem. 244 (2006) 179-182.
-
[17] T. Akiyama, K. Matsuda, K. Fuchibe, HCl-catalyzed stereoselective Mannich reaction in H2O-SDS system, Synlett (2005) 322-324.[17] T. Akiyama, K. Matsuda, K. Fuchibe, HCl-catalyzed stereoselective Mannich reaction in H2O-SDS system, Synlett (2005) 322-324.
-
[18] K. Matsuda, Y. Mori, S. Kobayashi, Three-component carbon-carbon bond-forming reactions catalyzed by a Brønsted acid-surfactant-combined catalyst in water, Tetrahedron 57 (2001) 2537-2544.[18] K. Matsuda, Y. Mori, S. Kobayashi, Three-component carbon-carbon bond-forming reactions catalyzed by a Brønsted acid-surfactant-combined catalyst in water, Tetrahedron 57 (2001) 2537-2544.
-
[19] M.L. Kantam, C.V. Rajasekhar, G. Gopikrishna, K.R. Reddy, B.M. Choudary, Proline catalyzed two-component, three-component and self-asymmetric Mannich reactions promoted by ultrasonic conditions, Tetrahedron Lett. 47 (2006) 5965-5967.[19] M.L. Kantam, C.V. Rajasekhar, G. Gopikrishna, K.R. Reddy, B.M. Choudary, Proline catalyzed two-component, three-component and self-asymmetric Mannich reactions promoted by ultrasonic conditions, Tetrahedron Lett. 47 (2006) 5965-5967.
-
[20] M.M. Heravi, M. Zakeri, N. Mohammadi, Guanidine hydrochloride: an active and simple catalyst for Mannich type reaction in solvent-free condition, Chin. Chem. Lett. 22 (2011) 797-800.[20] M.M. Heravi, M. Zakeri, N. Mohammadi, Guanidine hydrochloride: an active and simple catalyst for Mannich type reaction in solvent-free condition, Chin. Chem. Lett. 22 (2011) 797-800.
-
[21] Y. Dai, B.D. Li, H.D. Quan, C.X. Liu, CeCl3·7H2O as an efficient catalyst for one-pot synthesis of β-amino ketones by three-component Mannich reaction, Chin. Chem. Lett. 21 (2010) 31-34.[21] Y. Dai, B.D. Li, H.D. Quan, C.X. Liu, CeCl3·7H2O as an efficient catalyst for one-pot synthesis of β-amino ketones by three-component Mannich reaction, Chin. Chem. Lett. 21 (2010) 31-34.
-
[22] S. Iimura, D. Nobutou, K. Manabe, S. Kobayashi, Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst, Chem. Commun. (2003) 1644-1645.[22] S. Iimura, D. Nobutou, K. Manabe, S. Kobayashi, Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst, Chem. Commun. (2003) 1644-1645.
-
[23] N. Azizi, L. Torkiyan, M.R. Saidi, Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids, Org. Lett. 8 (2006) 2079-2082.[23] N. Azizi, L. Torkiyan, M.R. Saidi, Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids, Org. Lett. 8 (2006) 2079-2082.
-
[24] R. Wang, B.G. Li, T.K. Huang, L. Shi, X.X. Lu, NbCl5-catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds, Tetrahedron Lett. 48 (2007) 2071-2073.[24] R. Wang, B.G. Li, T.K. Huang, L. Shi, X.X. Lu, NbCl5-catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds, Tetrahedron Lett. 48 (2007) 2071-2073.
-
[25] L.M. Wang, J.W. Han, J. Sheng, H. Tian, Z.Y. Fan, Rare earth perfluorooctanoate[25] L.M. Wang, J.W. Han, J. Sheng, H. Tian, Z.Y. Fan, Rare earth perfluorooctanoate
-
[26]
[RE(PFO)3] catalyzed one-pot Mannich reaction: three component synthesis of bamino carbonyl compounds, Catal. Commun. 6 (2005) 201-204.[RE(PFO)3] catalyzed one-pot Mannich reaction: three component synthesis of bamino carbonyl compounds, Catal. Commun. 6 (2005) 201-204.
-
[26] L.M. Wang, J.W. Han, J. Sheng, Z.Y. Fan, H. Tian, Yb(OTf)3 catalyzed Mannich reaction of acetophe-none with aromatic aldehydes and aromatic amines: three component one-pot synthesis of β-amino ketone derivatives, Chin. J. Org. Chem. 25 (2005) 591-594.[26] L.M. Wang, J.W. Han, J. Sheng, Z.Y. Fan, H. Tian, Yb(OTf)3 catalyzed Mannich reaction of acetophe-none with aromatic aldehydes and aromatic amines: three component one-pot synthesis of β-amino ketone derivatives, Chin. J. Org. Chem. 25 (2005) 591-594.
-
[27] Y.G. Wang, Y.Y. Yang, W.G. Shou, Synthesis of β-amino carbonyl compounds via a Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds, Tetrahedron 62 (2006) 10079-11086.[27] Y.G. Wang, Y.Y. Yang, W.G. Shou, Synthesis of β-amino carbonyl compounds via a Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds, Tetrahedron 62 (2006) 10079-11086.
-
[28] Y.G. Wang, Y.Y. Yang, W.G. Shou, An efficient synthesis of β-amino esters via Zn(OTf)2-catalyzed Mannich-type reaction, Tetrahedron Lett. 47 (2006) 1845- 1847.[28] Y.G. Wang, Y.Y. Yang, W.G. Shou, An efficient synthesis of β-amino esters via Zn(OTf)2-catalyzed Mannich-type reaction, Tetrahedron Lett. 47 (2006) 1845- 1847.
-
[29] H. Li, H. Zeng, H. Shao, Bismuth (ⅡI) chloride-catalyzed one-pot Mannich reaction: three-component synthesis of β-amino carbonyl compounds, Tetrahedron Lett. 50 (2009) 6858-6860.[29] H. Li, H. Zeng, H. Shao, Bismuth (ⅡI) chloride-catalyzed one-pot Mannich reaction: three-component synthesis of β-amino carbonyl compounds, Tetrahedron Lett. 50 (2009) 6858-6860.
-
[30] Z. Li, X.L. Ma, J. Liu, et al., Silica-supported aluminum chloride: a recyclable and reusable catalyst for one-pot three-component Mannich-type reactions, J. Mol. Catal. A: Chem. 272 (2007) 132-135.[30] Z. Li, X.L. Ma, J. Liu, et al., Silica-supported aluminum chloride: a recyclable and reusable catalyst for one-pot three-component Mannich-type reactions, J. Mol. Catal. A: Chem. 272 (2007) 132-135.
-
[31] H. Wu, Y. Shen, L. Fan, et al., Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid, Tetrahedron 63 (2007) 2404-2408.[31] H. Wu, Y. Shen, L. Fan, et al., Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid, Tetrahedron 63 (2007) 2404-2408.
-
[32] X.C. Wang, L.J. Zhang, Z. Zhang, Z.J. Quan, PEG-OSO3H as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction in PEG-H2O, Chin. Chem. Lett. 23 (2012) 423-426.[32] X.C. Wang, L.J. Zhang, Z. Zhang, Z.J. Quan, PEG-OSO3H as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction in PEG-H2O, Chin. Chem. Lett. 23 (2012) 423-426.
-
[33] Q.H. Zhang, S.G. Zhang, Y.Q. Deng, Recent advances in ionic liquid catalysis, Green Chem. 13 (2011) 2619-2637.[33] Q.H. Zhang, S.G. Zhang, Y.Q. Deng, Recent advances in ionic liquid catalysis, Green Chem. 13 (2011) 2619-2637.
-
[34] D. Chaturvedi, Recent developments on task specific ionic liquids, Curr. Org. Chem. 15 (2011) 1236-1248.[34] D. Chaturvedi, Recent developments on task specific ionic liquids, Curr. Org. Chem. 15 (2011) 1236-1248.
-
[35] J.P. Hallett, T. Welton, Room-temperature ionic liquids: solvents for synthesis and catalysis, Chem. Rev. 111 (2011) 3508-3576.[35] J.P. Hallett, T. Welton, Room-temperature ionic liquids: solvents for synthesis and catalysis, Chem. Rev. 111 (2011) 3508-3576.
-
[36] L. Gharnati, O. Walter, U. Arnold, M. Döring, Guanidinium-based phosphotungstates and ionic liquids as catalysts and solvents for the epoxidation of olefins with hydrogen peroxide, Eur. J. Inorg. Chem. (2011) 2756-2762.[36] L. Gharnati, O. Walter, U. Arnold, M. Döring, Guanidinium-based phosphotungstates and ionic liquids as catalysts and solvents for the epoxidation of olefins with hydrogen peroxide, Eur. J. Inorg. Chem. (2011) 2756-2762.
-
[37] H. Li, Y.X. Qiao, L. Hua, et al., Imidazolium polyoxometalate: an ionic liquid catalyst for esterification and oxidative esterification, Chem. Cat. Chem. 2 (2010) 1165-1170.[37] H. Li, Y.X. Qiao, L. Hua, et al., Imidazolium polyoxometalate: an ionic liquid catalyst for esterification and oxidative esterification, Chem. Cat. Chem. 2 (2010) 1165-1170.
-
[38] Y.X. Qiao, Z.S. Hou, H. Li, et al., Polyoxometalate-based protic alkylimidazolium salts as reaction-induced phase-separation catalysts for olefin epoxidation, Green Chem. 11 (2009) 1955-1960.[38] Y.X. Qiao, Z.S. Hou, H. Li, et al., Polyoxometalate-based protic alkylimidazolium salts as reaction-induced phase-separation catalysts for olefin epoxidation, Green Chem. 11 (2009) 1955-1960.
-
[39] Y. Leng, J. Wang, D. Zhu, et al., Heteropolyanion-based ionic liquids: reactioninduced self-separation catalysts for esterification, Angew. Chem. Int. Ed. 48 (2009) 168-171.[39] Y. Leng, J. Wang, D. Zhu, et al., Heteropolyanion-based ionic liquids: reactioninduced self-separation catalysts for esterification, Angew. Chem. Int. Ed. 48 (2009) 168-171.
-
[40] Y.Leng,J.Wang,D.Zhu,Y.Wu,P.Zhao,Sulfonatedorganicheteropolyacidsalts:recyclable green solid catalysts for esterifications, J.Mol. Catal. A: Chem. 313 (2009) 1-6.[40] Y.Leng,J.Wang,D.Zhu,Y.Wu,P.Zhao,Sulfonatedorganicheteropolyacidsalts:recyclable green solid catalysts for esterifications, J.Mol. Catal. A: Chem. 313 (2009) 1-6.
-
[41] W. Zhang, Y. Leng, D. Zhu, Y. Wu, J. Wang, Phosphotungstic acid salt of triphenyl( 3-sulfopropyl)phosphonium: an efficient and reusable solid catalyst for esterification, Catal. Commun. 11 (2009) 151-154.[41] W. Zhang, Y. Leng, D. Zhu, Y. Wu, J. Wang, Phosphotungstic acid salt of triphenyl( 3-sulfopropyl)phosphonium: an efficient and reusable solid catalyst for esterification, Catal. Commun. 11 (2009) 151-154.
-
[42] Y. Leng, P.P. Jiang, J. Wang, A novel Brønsted acidic heteropolyanion-based polymeric hybrid catalyst for esterification, Catal. Commun. 25 (2012) 41-44.[42] Y. Leng, P.P. Jiang, J. Wang, A novel Brønsted acidic heteropolyanion-based polymeric hybrid catalyst for esterification, Catal. Commun. 25 (2012) 41-44.
-
[43] J. Yuan, M. Antonietti, Poly(ionic liquid)s: polymers expanding classical property profiles, Polymer 52 (2011) 1469-1482.[43] J. Yuan, M. Antonietti, Poly(ionic liquid)s: polymers expanding classical property profiles, Polymer 52 (2011) 1469-1482.
-
[44] Z.J. Xu, H. Wan, J.M. Miao, M.J. Han, C. Yang, G.F. Guan, Reusable and efficient polystyrene-supported acidic ionic liquid catalyst for esterifications, J. Mol. Catal. A: Chem. 332 (2010) 152-157.[44] Z.J. Xu, H. Wan, J.M. Miao, M.J. Han, C. Yang, G.F. Guan, Reusable and efficient polystyrene-supported acidic ionic liquid catalyst for esterifications, J. Mol. Catal. A: Chem. 332 (2010) 152-157.
-
[45] K.M. Docherty, J.K. Dixon, C.F. Kulpa, Biodegradability of imidazolium and pyridinium ionic liquids by an activated sludge microbial community, Biodegradation 18 (2007) 481-493.[45] K.M. Docherty, J.K. Dixon, C.F. Kulpa, Biodegradability of imidazolium and pyridinium ionic liquids by an activated sludge microbial community, Biodegradation 18 (2007) 481-493.
-
[46] J.K. Wang, Y.X. Zong, R.G. Fu, Y.Y. Niu, G.R. Yue, Z.J. Quan, X.C. Wang, Y. Pan, Poly(4- vinylpyridine) supported acidic ionic liquid: a novel solid catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones under ultrasonic irradiation, Ultrason. Sonochem. 21 (2014) 29-34.[46] J.K. Wang, Y.X. Zong, R.G. Fu, Y.Y. Niu, G.R. Yue, Z.J. Quan, X.C. Wang, Y. Pan, Poly(4- vinylpyridine) supported acidic ionic liquid: a novel solid catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones under ultrasonic irradiation, Ultrason. Sonochem. 21 (2014) 29-34.
-
[47] Y.X. Zong, Y. Zhao, W.C. Luo, X.H. Yu, J.K. Wang, Y. Pan, Highly efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropoly acids in water, Chin. Chem. Lett. 21 (2010) 778-781.[47] Y.X. Zong, Y. Zhao, W.C. Luo, X.H. Yu, J.K. Wang, Y. Pan, Highly efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropoly acids in water, Chin. Chem. Lett. 21 (2010) 778-781.
-
[48] Y.X. Zong, J.K. Wang, Y.Y. Niu, Z.L. Li, Z.E. Song, Z.J. Quan, X.C. Wang, G.R. Yue, Y. Pan, PEG-SO3H as an efficient and reusable catalyst for chemoselective synthesis of 1,1-diacetates, Chin. Chem. Lett. 24 (2013) 140-142.[48] Y.X. Zong, J.K. Wang, Y.Y. Niu, Z.L. Li, Z.E. Song, Z.J. Quan, X.C. Wang, G.R. Yue, Y. Pan, PEG-SO3H as an efficient and reusable catalyst for chemoselective synthesis of 1,1-diacetates, Chin. Chem. Lett. 24 (2013) 140-142.
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