Citation: Wen-You Li, Ying-Xiao Zong, Jun-Ke Wang, Yu-Ying Niu. Sulfonated poly(4-vinylpyridine) heteropolyacid salts：A reusable green solid catalyst for Mannich reaction[J]. Chinese Chemical Letters, ;2014, 25(4): 575-578. doi: 10.1016/j.cclet.2013.11.022 shu

Sulfonated poly(4-vinylpyridine) heteropolyacid salts：A reusable green solid catalyst for Mannich reaction

Wen-You Li ^b ,
Ying-Xiao Zong ^a,c,, ,
Jun-Ke Wang ^a,b,, ,
Yu-Ying Niu ^a

1.
a Key Laboratory of Hexi Corridor Resources Utilization of Gansu Universities, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, China;
2.
b Department of Chemical Engineering, Jiuquan Vacational and Technical College, Jiuquan 735009, China;
3.
c Gansu Engineering Laboratory of Applied Mycology, Hexi University, Zhangye 734000, China

Corresponding author: Ying-Xiao Zong, Jun-Ke Wang,
Received Date: 22 September 2013
Available Online: 5 November 2013
Fund Project: This work was financially supported by Key Laboratory of Hexi Corridor Resources Utilization of Gansu Universities (No. XZ1011) (No. XZ1011) the President's Funds of Hexi University (No. XZ-2009-9) (No. XZ-2009-9)

Sulfonated poly(4-vinylpyridine) heteropolyacid salts acted as a heterogeneous catalyst to effectively catalyze the one-pot synthesis of β-amino carbonyl compounds via the Mannich reaction between aromatic aldehydes, aromatic ketone, and aromatic amines. In addition, the catalyst could be easily recovered by the filtration and reused six times without significant loss of catalytic activity.
- Mannich reaction,
- Heteropolyacid,
- Poly(4-vinylpyridine),
- Heterogeneous catalyst
1. [1]
  [1] M. Arend, B. Westermann, N. Risch, Modern variants of the Mannich reaction, Angew. Chem. Int. Ed. 37 (1998) 1044-1070.
2. [2]
  [2] S. Kobayashi, H. Ishitani, Catalytic enantioselective addition to imines, Chem. Rev. 99 (1999) 1069-1094.
3. [3]
  [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. [4]
  [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. [5]
  [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. [6]
  [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. [7]
  [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. [8]
  [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. [9]
  [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. [10]
  [10] B. List, The direct catalytic asymmetric three-component Mannich reaction, J. Am. Chem. Soc. 122 (2000) 9336-9337.
11. [11]
  [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. [12]
  [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. [13]
  [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. [14]
  [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. [15]
  [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. [16]
  [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. [17]
  [17] T. Akiyama, K. Matsuda, K. Fuchibe, HCl-catalyzed stereoselective Mannich reaction in H₂O-SDS system, Synlett (2005) 322-324.
18. [18]
  [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. [19]
  [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. [20]
  [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. [21]
  [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. [22]
  [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. [23]
  [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. [24]
  [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. [25]
  [25] L.M. Wang, J.W. Han, J. Sheng, H. Tian, Z.Y. Fan, Rare earth perfluorooctanoate
26. [26]
  [RE(PFO)₃] catalyzed one-pot Mannich reaction: three component synthesis of bamino carbonyl compounds, Catal. Commun. 6 (2005) 201-204.
27. [27]
  [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.
28. [28]
  [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.
29. [29]
  [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.
30. [30]
  [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.
31. [31]
  [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.
32. [32]
  [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.
33. [33]
  [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.
34. [34]
  [33] Q.H. Zhang, S.G. Zhang, Y.Q. Deng, Recent advances in ionic liquid catalysis, Green Chem. 13 (2011) 2619-2637.
35. [35]
  [34] D. Chaturvedi, Recent developments on task specific ionic liquids, Curr. Org. Chem. 15 (2011) 1236-1248.
36. [36]
  [35] J.P. Hallett, T. Welton, Room-temperature ionic liquids: solvents for synthesis and catalysis, Chem. Rev. 111 (2011) 3508-3576.
37. [37]
  [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.
38. [38]
  [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.
39. [39]
  [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.
40. [40]
  [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.
41. [41]
  [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.
42. [42]
  [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.
43. [43]
  [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.
44. [44]
  [43] J. Yuan, M. Antonietti, Poly(ionic liquid)s: polymers expanding classical property profiles, Polymer 52 (2011) 1469-1482.
45. [45]
  [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.
46. [46]
  [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.
47. [47]
  [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.
48. [48]
  [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.
49. [49]
  [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.
1. [1]
  Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS₂/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
2. [2]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
3. [3]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
4. [4]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
5. [5]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
6. [6]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
7. [7]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
8. [8]
  Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2023.100199
9. [9]
  Mengxiang Zhu , Tao Ding , Yunzhang Li , Yuanjie Peng , Ruiping Liu , Quan Zou , Leilei Yang , Shenglei Sun , Pin Zhou , Guosheng Shi , Dongting Yue . Graphene controlled solid-state growth of oxygen vacancies riched V₂O₅ catalyst to highly activate Fenton-like reaction. Chinese Chemical Letters, 2024, 35(12): 109833-. doi: 10.1016/j.cclet.2024.109833
10. [10]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
11. [11]
  Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe₂O₄@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
12. [12]
  Jin Long , Xingqun Zheng , Bin Wang , Chenzhong Wu , Qingmei Wang , Lishan Peng . Improving the electrocatalytic performances of Pt-based catalysts for oxygen reduction reaction via strong interactions with single-CoN₄-rich carbon support. Chinese Chemical Letters, 2024, 35(5): 109354-. doi: 10.1016/j.cclet.2023.109354
13. [13]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
14. [14]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
15. [15]
  Xiaoyu Zhang , Xin Yu . Solar-powered heterogeneous water disinfection nano-system. Chinese Journal of Structural Chemistry, 2025, 44(3): 100439-100439. doi: 10.1016/j.cjsc.2024.100439
16. [16]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
17. [17]
  Xueyang Zhao , Bangwei Deng , Hongtao Xie , Yizhao Li , Qingqing Ye , Fan Dong . Recent process in developing advanced heterogeneous diatomic-site metal catalysts for electrochemical CO₂ reduction. Chinese Chemical Letters, 2024, 35(7): 109139-. doi: 10.1016/j.cclet.2023.109139
18. [18]
  Ruonan Guo , Heng Zhang , Changsheng Guo , Ningqing Lv , Beidou Xi , Jian Xu . Degradation of neonicotinoids with different molecular structures in heterogeneous peroxymonosulfate activation system through different oxidation pathways. Chinese Chemical Letters, 2024, 35(9): 109413-. doi: 10.1016/j.cclet.2023.109413
19. [19]
  Ji Chen , Yifan Zhao , Shuwen Zhao , Hua Zhang , Youyu Long , Lingfeng Yang , Min Xi , Zitao Ni , Yao Zhou , Anran Chen . Heterogeneous bimetallic oxides/phosphides nanorod with upshifted d band center for efficient overall water splitting. Chinese Chemical Letters, 2024, 35(9): 109268-. doi: 10.1016/j.cclet.2023.109268
20. [20]
  Xin He , Feng Liu , Tao Tu . Double redox-mediated intrinsic semiconductor photocatalysis: Practical semi-heterogeneous synthesis. Chinese Chemical Letters, 2025, 36(3): 110621-. doi: 10.1016/j.cclet.2024.110621

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(690)
HTML views(28)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142