Citation: Manpreet Kaur, Sahil Sharma, Preet M. S. Bedi. Silica supported Brönsted acids as catalyst in organic transformations: A comprehensive review[J]. Chinese Journal of Catalysis, ;2015, 36(4): 520-549. doi: 10.1016/S1872-2067(14)60299-0 shu

Silica supported Brönsted acids as catalyst in organic transformations: A comprehensive review

1.
Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar-143005, Punjab, India

Corresponding author: Sahil Sharma,
Received Date: 11 November 2014
Available Online: 13 January 2015
Fund Project:

Brönsted acid catalysts have been used in a number of organic transformations. To overcome limitations, such as toxicity, volatility, high price and hazardous nature of the conventional methods, the catalysts are adsorbed on silica gel to give the benefits and advantages of ready availability, simple work-up procedure, long catalytic life, environment-friendliness, good to excellent yields and recyclability. The uses of such catalysts have gained importance worldwide. This article describes some of the important silicated catalysts, namely, heteropolyacids, polyphosphoric acid, perchloric acid, fluoroboric acid, and silicated sulphuric acid. These catalysts have been used in a number of organic reactions to yield compounds that are important in the chemical and pharmaceutical industries. We summarize the beneficial effects of these catalysts and the reports that have been published on them in the past several years. In the present review, the description of the catalysts are introduced followed by a recent research history, and a comparison between the silica supported catalysts and other (polymer) supported catalysts. The article ends up giving the advantages of these catalytic systems over the conventional catalyst.
- Brönsted acids,
- Silicated catalysts,
- Recyclability,
- Chemoselectivity,
- Conventional
1. [1]
  [1] Salehi P, Zolfigol M A, Fard M A B. Tetrahedron Lett, 2003, 44: 2889
2. [2]
  [2] Bandgar B P, Patil A V. Tetrahedron Lett, 2007, 48: 173
3. [3]
  [3] Kamble V T, Bandgar B P, Mule D B, Joshi N S. J Mol Catal A, 2007, 268: 70
4. [4]
  [4] Singh D U, Singh P R, Samant S D. Tetrahedron Lett, 2004, 45: 4805
5. [5]
  [5] Yadav J S, Satyanarayana M, Balanarsaiah E, Raghavendra S. Tetrahedron Lett, 2006, 47: 6095
6. [6]
  [6] Rafiee E, Rashidzadeh S, Azad A. J Mol Catal A, 2007, 261: 49
7. [7]
  [7] Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Hojati S F. Polyhedron, 2008, 27: 750
8. [8]
  [8] Khan A B, Choudhury L H, Ghosh S. J Mol Catal A, 2006, 255: 230
9. [9]
  [9] Dara S, Saikam V, Yadav M, Singh P P, Vishwakarma R A. Carbohydr Res, 2014, 391: 93
10. [10]
  [10] Das B, Venkateswarlu K, Majhi A, Reddy M R, Reddy K N, Rao Y K, Ravikumar K, Sridhar B. J Mol Catal A, 2006, 246: 276
11. [11]
  [11] Kiasat A R, Zayadi M, Mehrjardi M F. Chin Chem Lett, 2008, 19: 665
12. [12]
  [12] Eshghi H, Hassankhani A. J Korean Chem Soc, 2007, 51: 361
13. [13]
  [13] Rafiee E, Shahbazi F. J Mol Catal A, 2006, 250: 57
14. [14]
  [14] Lana E J L, da Silva Rocha K A, Kozhevnikov I V, Gusevskaya E V. J Mol Catal A, 2006, 259: 99
15. [15]
  [15] Rafiee E, Joshaghani M, Tork F, Fakhri A, Eavani S. J Mol Catal A, 2008, 283: 1
16. [16]
  [16] Rafiee E, Paknezhad F, Shahebrahimi S, Joshaghani M, Eavani S, Rashidzadeh S. J Mol Catal A, 2008, 282: 92
17. [17]
  [17] Yadav J S, Reddy B V S, Pandurangam T, Rao K V R, Praneeth K, Kumar G G K S N, Madavi C, Kunwar A C. Tetrahedron Lett, 2008, 49: 4296
18. [18]
  [18] Liu Y, Xu L, Xu B, Li Z, Jia L, Guo W. J Mol Catal A, 2009, 297: 86
19. [19]
  [19] Rafiee E, Eavani S, Rashidzadeh S, Joshaghani M. Inorg Chim Acta, 2009, 362: 3555
20. [20]
  [20] Parida K M, Rana S, Mallick S, Rath D. J Colloid Interface Sci, 2010, 350: 132
21. [21]
  [21] Rafiee E, Khodayaria M, Shahebrahimia S, Joshaghania M. J Mol Catal A, 2011, 351: 204
22. [22]
  [22] Murugan K, Srimurugan S, Chen C. Tetrahedron, 2011, 67: 5621
23. [23]
  [23] Liu P N, Xia F, Zhao Z L, Wang Q W, Pen Y J. Tetrahedron Lett, 2011, 52: 6113
24. [24]
  [24] Rafiee E, Khodayaria M, Kahrizia M, Tayebeeb R. J Mol Catal A, 2012, 358: 121
25. [25]
  [25] Ghanbaripour R, Mohammadpoor-Baltork I, Moghadam M, Khosropour A R, Tangestaninejad S, Mirkhani V. Polyhedron, 2012, 31: 721
26. [26]
  [26] Xie S L, Hui Y H, Long X J, Wang C C, Xie Z F. Chin Chem Lett, 2013, 24: 28
27. [27]
  [27] Ahmed A I, Samra S E, El-Hakama S A, Khderb A S, El-Shenawya H Z, Abo El-Yazeeda W S. Appl Surf Sci, 2013, 282: 217
28. [28]
  [28] Kantevari S, Bantu R, Nagarapu L. J Mol Catal A, 2007, 269: 53
29. [29]
  [29] Shaterian H R, Hosseinian A, Ghashang M. Synth Commun, 2008, 38: 3375
30. [30]
  [30] Shaterian H R, Hosseinian A, Ghashang M. Arkivoc, 2009, (ii): 59
31. [31]
  [31] Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
32. [32]
  [32] Khojastehnezhad A, Moeinpour F, Davoodnia A. Chin Chem Lett, 2011, 22: 807
33. [33]
  [33] Davoodnia A, Allameh S, Fazli S, Hoseini N T. Chem Pap, 2011, 65: 714
34. [34]
  [34] Itoh K, Aoyama T, Satoh H, Fujii Y, Sakamak H, Takido T, Kodomari M. Tetrahedron Lett, 2011, 52: 6892
35. [35]
  [35] Bamoniri A, Mirjalili B F, Nazemian S. J Nano Struct, 2012, 2: 101
36. [36]
  [36] Manolov S, Nikolova S, Ivanov I. Molecules, 2013, 18: 1869
37. [37]
  [37] Shafiee M R M. J Saudi Chem Soc, 2014, 18: 115
38. [38]
  [38] Misra A K, Tiwari P, Madhusudan S K. Carbohydr Res, 2005, 340: 325
39. [39]
  [39] Mukhopahyay B, Russell D A, Field R A. Carbohydr Res, 2005, 340: 1075
40. [40]
  [40] Du Y, Wei G, Cheng S, Hua Y, Linhardt R J. Tetrahedron Lett, 2006, 47: 307
41. [41]
  [41] Tiwari P, Misra A K. Tetrahedron Lett, 2006, 47: 3573
42. [42]
  [42] Agnihotri G, Misra A K. Tetrahedron Lett, 2006, 47: 3653
43. [43]
  [43] Bigdeli M A, Heravi M M, Mahdavinia G H. J Mol Catal A, 2007, 275: 25
44. [44]
  [44] Kantevari S, Vuppalapati S V N, Biradar D O, Nagarapu L. J Mol Catal A, 2007, 266: 109
45. [45]
  [45] Narasimhulu M, Reddy T S, Mahesh K C, Prabhakar P, Rao C B, Venkateswarlu Y. J Mol Catal A, 2007, 266: 114
46. [46]
  [46] Nagarapu L, Paparaju V, Pathuri G, Kantevari S, Pakkiru R R, Kamalla R. J Mol Catal A, 2007, 267: 53
47. [47]
  [47] Khatik G L, Sharma G, Kumar R, Chakraborti A K. Tetrahedron, 2007, 63: 1200
48. [48]
  [48] Kantevari S, Bantu R, Nagarapu L. J Mol Catal A, 2007, 269: 53
49. [49]
  [49] Shaterian H R, Shahrekipoor F, Ghashang M. J Mol Catal A, 2007, 272: 142
50. [50]
  [50] Das B, Venkateswarlu K, Suneel K, Majhi A. Tetrahedron Lett, 2007, 48: 5371
51. [51]
  [51] Modarresi-Alam A R, Khamooshi F, Nasrollahzadeh M, Amirazizi H A. Tetrahedron, 2007, 63: 8723
52. [52]
  [52] Bigdeli M A, Nemati F, Mahdavinia G H. Tetrahedron Lett, 2007, 48: 6801
53. [53]
  [53] Shaterian H R, Yarahmadi H, Ghashang M. Tetrahedron, 2008, 64: 1263
54. [54]
  [54] Mahdavinia G H, Bigdeli M A, Heravi M M. Chin Chem Lett, 2008, 19: 1171
55. [55]
  [55] Kumar A, Sharma S, Maurya R A. Tetrahedron Lett, 2009, 50: 5937
56. [56]
  [56] Ludek O R, Gu W, Gildersleeve J C. Carbohydr Res, 2010, 345: 2074
57. [57]
  [57] Maghsoodlou M T, Habibi-Khorassani S M, Heydari R, Hazeri N, Sajadikhah S S, Rostamizadeh M. Arab J Chem, 2011, 4: 481
58. [58]
  [58] Du T J, Wu Q P, Liu H X, Chen X, Shu Y N, Xi X D, Zhang Q S, Li Y Z. Tetrahedron, 2011, 67: 1096
59. [59]
  [59] Das B, Reddy P R, Sudhakar C, Lingaiah M. Tetrahedron Lett, 2011, 52: 3521
60. [60]
  [60] Murugan K, Chen C. Tetrahedron Lett, 2011, 52: 5827
61. [61]
  [61] Chun Y, Yan S, Li X, Ding N, Zhang W, Wang P, Li M, Li Y. Tetrahedron Lett, 2011, 52: 6196
62. [62]
  [62] Ansari M I, Hussain M K, Yadav N, Gupta P K, Hajela K. Tetrahedron Lett, 2012, 53: 2063
63. [63]
  [63] Chakraborti A K, Gulhane R. Tetrahedron Lett, 2003, 44: 3521
64. [64]
  [64] Bandgar B P, Patil A V, Chavan O S. J Mol Catal A, 2006, 256: 99
65. [65]
  [65] Kamble V T, Bandgar B P, Muley D B, Joshi N S. J Mol Catal A, 2007, 268: 70
66. [66]
  [66] Bandgar B P, Patil A V. Tetrahedron Lett, 2007, 48: 173
67. [67]
  [67] Bandgar B P, Patil A V, Kamble V T, Totre J V. J Mol Catal A, 2007, 273: 114
68. [68]
  [68] Sharma G, Kumar R, Chakraborti A K. Tetrahedron Lett, 2008, 49: 4272
69. [69]
  [69] Bandgar B P, Gawande S S, Warangkar S C, Totre J V. Bioorg Med Chem, 2010, 18: 3618
70. [70]
  [70] Sharma S, Sharma K, Ojha R, Kumar D, Singh G, Nepali K, Bedi P M S. Bioorg Med Chem Lett, 2014, 24: 495
71. [71]
  [71] Shukla S, Kumar D, Ojha R, Gupta M K, Nepali K, Bedi P M S. Arch Pharm, 2014, 347: 486
72. [72]
  [72] Rajput V K, Roy B, Mukhopadhyay B. Tetrahedron Lett, 2006, 47: 6987
73. [73]
  [73] Niknam K, Zolfigol M A, Khorramabadi-Zad A, Zare R, Shayegh M. Catal Commun, 2006, 7: 494
74. [74]
  [74] Gawande M B, Polshettiwar V, Varma R S, Jayarama R V. Tetrahedron Lett, 2007, 48: 8170
75. [75]
  [75] Roy B, Mukhopadhyay B. Tetrahedron Lett, 2007, 48: 3783
76. [76]
  [76] Zhou J F, Chen X, Wang Q B, Zhang B, Zhang L Y, Yusulf A, Wang Z F, Zhang J B, Tang J. Chin Chem Lett, 2010, 21: 922
77. [77]
  [77] Safari J, Banitaba S H, Khalili S D. Arab J Chem, 2011, 4: 11
78. [78]
  [78] Modarresi-Alam A R, Inaloo I D, Kleinpeter E. J Mol Struct, 2012, 1024: 156
79. [79]
  [79] Bakherad M, Keivanloo A, Siavashi M, Omidian M. Chin Chem Lett, 2014, 25: 149
80. [80]
  [80] Zolfigol M A. Tetrahedron, 2001, 57: 9509
81. [81]
  [81] Pore D M, Soudagar M S, Desai U V, Thopatea T S, Wadagaonkar P P. Tetrahedron Lett, 2006, 47: 9325
82. [82]
  [82] Niknam K, Karami B, Zolfigol M A. Catal Commun, 2007, 8: 1427
83. [83]
  [83] Wu H, Shen Y, Fan L Y, Wan Y, Zhang P, Chen C F, Wang W X. Tetrahedron, 2007, 63: 2404
84. [84]
  [84] Modarresi-Alam A R, Nasrollahzadeh M, Khamooshi F. Arkivoc, 2007, 16: 238
85. [85]
  [85] Khalafi-Nezhad A, Parhami A, Navid M, Rad S, Zolfigol M A, Zare A. Tetrahedron Lett, 2007, 48: 5219
86. [86]
  [86] Mohammadpoor-Baltork I, Mirkhani V, Moghadam M, Tangestaninejad S, ZolFigol M A, Alibeik M A, Khosropour A R, Kargar H, Hojati S F. Catal Commun, 2008, 9: 894
87. [87]
  [87] Shaterian H R, Ghashang M, Feyzi M. Appl Catal A, 2008, 345: 128
88. [88]
  [88] Massah A R, Adibi H, Khodarahmi R, Abiri R, Majnooni M B, Shahidi S, Asadi B, Mehrabib M, Zolfigol M A. Bioorg Med Chem, 2008, 16: 5465
89. [89]
  [89] Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirinid F, Khoramabadi-Zada A. J Chin Chem Soc, 2008, 55: 885
90. [90]
  [90] Zolfigol M A, Salehi P, Shiri M, Sayadi A, Abdoli A, Keypour H, Rezaeivala M, Niknam K, Kolvari E. Mol Divers, 2008, 12: 203
91. [91]
  [91] Wang Y, Yuan Y Q, Guo S R. Molecules, 2009, 14: 4779
92. [92]
  [92] Zarei A, Hajipour A R, Khazdooz L, Mirjalili B F, Chermahini A N. Dyes Pigm, 2009, 81: 240
93. [93]
  [93] Veisi H. Tetrahedron Lett, 2010, 51: 2109
94. [94]
  [94] Li J T, Meng X T, Bai B, Xuan M. Sun Ultrason Sonochem, 2010, 17: 14
95. [95]
  [95] Niknam K, Mirzaee S. Synth Commun, 2011, 41: 2403
96. [96]
  [96] Mansoor S S, Aswin K, Logaiya K, Sudhan S P N. J Taibah Univ Science, 2014, 8: 265
97. [97]
  [97] De Vos D, Vankelecom I F J, Jacobs P A eds. Chiral Catalyst Immobilization and Recycling. Weinheim: Wiley-VCH, 2000
98. [98]
  [98] Fan Q H, Wang R, Chan A S C. Bioorg Med Chem Lett, 2002, 12: 1867
99. [99]
  [99] Saluzzo C, Lamouille T, Herault D, Lemaire M. Bioorg Med Chem Lett, 2002, 12: 1841
100. [100]
  [100] Inamdar S M, More V K, MandalS K. Tetrahedron Lett, 2013, 54: 579
101. [101]
  [101] Pedrosa R, Andres J M, Gamarra A, Manzano R, Perez-Lopez C. Tetrahedron, 2013, 69: 10811
102. [102]
  [102] Movassagh B, Rezaei N. Tetrahedron, 2014, 70: 8885
103. [103]
  [103] Bodhak C, Kundu A, Pramanik A. Tetrahedron Lett, 2015, 56: 419
104. [104]
  [104] Yoon H J, Lee S M, Kim J H, Cho H J, Choi J W, Lee S H, Lee Y S. Tetrahedron Lett, 2008, 49: 3165
105. [105]
  [105] Guha N R, Bhattacherjee D, Das P. Tetrahedron Lett, 2014, 55: 2912
106. [106]
  [106] Kell R J, Hodge P, Nisar M, Watson D. Bioorg Med Chem Lett, 2002, 12: 1803
107. [107]
  [107] Salehi P, Zolfigol M A, Shirini F, Baghbanzadeh M. Curr Org Chem, 2006, 10: 2171
1. [1]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
2. [2]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
3. [3]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
4. [4]
  Junjie Duan , Dan Chen , Long Chen , Shuying Li , Ting Chen , Dong Wang . 2D hexagonal tessellations sustained by Br···Br/H contacts: From regular to semiregular to k-uniform tilings. Chinese Chemical Letters, 2025, 36(3): 110445-. doi: 10.1016/j.cclet.2024.110445
5. [5]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
6. [6]
  Hongmei Yu , Baoxi Zhang , Meiju Liu , Cheng Xing , Guorong He , Li Zhang , Ningbo Gong , Yang Lu , Guanhua Du . Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers. Chinese Chemical Letters, 2024, 35(5): 109032-. doi: 10.1016/j.cclet.2023.109032
7. [7]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
8. [8]
  Yanjing Li , Jiayin Li , Yuqi Chang , Yunfeng Lin , Lei Sui . Tetrahedral framework nucleic acids promote the proliferation and differentiation potential of diabetic bone marrow mesenchymal stem cell. Chinese Chemical Letters, 2024, 35(9): 109414-. doi: 10.1016/j.cclet.2023.109414
9. [9]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
10. [10]
  Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
11. [11]
  Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
12. [12]
  Xinyi Luo , Ke Wang , Yingying Xue , Xiaobao Cao , Jianhua Zhou , Jiasi Wang . Digital PCR-free technologies for absolute quantitation of nucleic acids at single-molecule level. Chinese Chemical Letters, 2025, 36(2): 109924-. doi: 10.1016/j.cclet.2024.109924
13. [13]
  Yutong Xiong , Ting Meng , Wendi Luo , Bin Tu , Shuai Wang , Qingdao Zeng . Molecular conformational effects on co-assembly systems of low-symmetric carboxylic acids investigated by scanning tunneling microscopy. Chinese Journal of Structural Chemistry, 2025, 44(2): 100511-100511. doi: 10.1016/j.cjsc.2025.100511
14. [14]
  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
15. [15]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
16. [16]
  Fanxin Kong , Hongzhi Wang , Huimei Duan . Inhibition effect of sulfation on Pt/TiO2 catalysts in methane combustion. Chinese Journal of Structural Chemistry, 2024, 43(5): 100287-100287. doi: 10.1016/j.cjsc.2024.100287
17. [17]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
18. [18]
  Pingfan Zhang , Shihuan Hong , Ning Song , Zhonghui Han , Fei Ge , Gang Dai , Hongjun Dong , Chunmei Li . Alloy as advanced catalysts for electrocatalysis: From materials design to applications. Chinese Chemical Letters, 2024, 35(6): 109073-. doi: 10.1016/j.cclet.2023.109073
19. [19]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
20. [20]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534

Get Citation

PDF

XML

Metrics

PDF Downloads(459)
Abstract views(643)
HTML views(10)

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