Citation: Nader Ghaffari Khaligh, Parisa Ghods Ghasem-Abadi. N-Sulfonic acid poly(4-vinylpyridinum) hydrogen sulfate as a novel, efficient, and reusable solid acid catalyst for acylation under solvent-free conditions[J]. Chinese Journal of Catalysis, ;2014, 35(7): 1126-1135. doi: 10.1016/S1872-2067(14)60052-8 shu

N-Sulfonic acid poly(4-vinylpyridinum) hydrogen sulfate as a novel, efficient, and reusable solid acid catalyst for acylation under solvent-free conditions

  • Corresponding author: Nader Ghaffari Khaligh, 
  • Received Date: 1 January 2014
    Available Online: 10 February 2014

  • N-Sulfonic acid poly(4-vinylpyridinum) hydrogen sulfate has been developed as a recyclable solid acid catalyst for the acetylation of alcohols, phenols, thiols, and amines, as well as the 1,1-diacetylation of aldehydes under solvent-free conditions at room temperature. The acetylated products were formed in good to excellent yields over short reaction times, and the catalyst could be readily recovered by filtration and used several times without any discernible loss in activity. The hydrogen sulfate anion of the catalytic system was found to play a critical role in enhancing the reaction time and yield of the acetylation reaction.
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    1. [1]

      [1] Smith K. Solid Supports and Catalysis in Organic Synthesis. New York: Ellis Horwood and PTR Prentice Hall, 1992

    2. [2]

      [2] Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513

    3. [3]

      [3] Turro N J. Tetrahedron, 1987, 43: 1589

    4. [4]

      [4] Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirini F, Khoramabadi-Zad A. J Chin Chem Soc, 2008, 55: 885

    5. [5]

      [5] Chehardoli G, Zolfigol M A, Faal-Rastegar T, Mallakpour S, Ghorbani-Choghamaranid A. J Chem Sci, 2009, 121: 441

    6. [6]

      [6] Khaligh N G, Shirini F. J Mol Catal A, 2011, 348: 20

    7. [7]

      [7] Khaligh N G. Ultrason Sonochem, 2012, 19: 736

    8. [8]

      [8] Khaligh N G. Tetrahedron Lett, 2012, 53: 1637

    9. [9]

      [9] Cole-Hamilton D J. Science, 2003, 299: 1702

    10. [10]

      [10] Curzons A, Constable C C, Cunningham V L. Clean Prod Process, 1999, 1: 82

    11. [11]

      [11] Tanaka K. Solvent-Free Organic Synthesis. Weinheim: Wiley-VCH, GmbH and KGaA, 2004

    12. [12]

      [12] Gani R, Jiménez-Gonzalez C, ten Kate A, Crafts P A, Powell M J, Powell L, Atherton J H, Cordiner J L. Chem Eng, 2006, 113: 30

    13. [13]

      [13] Shaabani A, Ghadari R, Rahmati A, Rezayan A H. J Iran Chem Soc, 2009, 6: 710

    14. [14]

      [14] Greene T W, Wuts P G M. Protective Groups in Organic Synthesis. 3rd Ed. New York: John Wiley and Sons, 1999. 306

    15. [15]

      [15] Otera J. Esterification: Methods, Reactions and Applications. Weinheim: Wiley-VCH, 2003

    16. [16]

      [16] Sun X L, Kai T, Takayanagi H, Furuhata K. Synlett, 1999: 1399

    17. [17]

      [17] Yadav J S, Narsaiah A V, Basak A K, Goud P R, Sreenu D, Nagaiah K. J Mol Catal A, 2006, 255: 78

    18. [18]

      [18] Scriven E F V. Chem Soc Rev, 1983, 12: 129

    19. [19]

      [19] Höfle G, Steglich V, Vorbrüggen H. Angew Chem Int Ed, 1978, 17: 569

    20. [20]

      [20] Cope A C, Herrich E C. Organic Synthesis Collective. Vol. IV. New York: Wiley, 1963. 304

    21. [21]

      [21] Li A X, Li T S, Ding T H. Chem Commun, 1997: 1389

    22. [22]

      [22] Hagiwara H, Morohashi K, Suzuki T, Ando M, Yamamoto I, Kato M. Synth Commun, 1998, 28: 2001

    23. [23]

      [23] Ballini R, Bosica G, Carloni S, Ciaralli L, Maggi R, Sartori G. Tetrahedron Lett, 1998, 39: 6049

    24. [24]

      [24] Niknam K, Saberi D. Appl Catal A, 2009, 366: 220

    25. [25]

      [25] Joseph J K, Jain S L, Sain B. J Mol Catal A, 2007, 267: 108

    26. [26]

      [26] Niknam K, Saberi D. Tetrahedron Lett, 2009, 50: 5210

    27. [27]

      [27] Shirini F, Zolfigol MA, Mohammadi K. Bull Korean Chem Soc, 2004, 25: 325

    28. [28]

      [28] Chakraborti A K, Gulhane R. Chem Commun, 2003: 1896

    29. [29]

      [29] Heravi M M, Behbahani F K, Bamoharram F F. J Mol Catal A, 2006, 253: 16

    30. [30]

      [30] Khaligh N G. J Mol Catal A, 2012, 363-364: 90

    31. [31]

      [31] Khaligh N G. RSC Adv, 2013, 3: 99

    32. [32]

      [32] Trost B M, Lee C B. J Am Chem Soc, 2001, 123: 3687

    33. [33]

      [33] Gregory M J. J Chem Soc B, 1970: 1201

    34. [34]

      [34] Sandberg M, Sydnes L K. Org Lett, 2000, 2: 687

    35. [35]

      [35] Held H, Rengstle A, Mayer D. In: Gerhartz W Ed. Ullman's Encyclopedia of Industrial Chemistry. 5th Ed. Vol. A1. New York: VCH, 1985. 68

    36. [36]

      [36] Freeman F, Karchefski E M. J Chem Eng Data, 1977, 22: 355

    37. [37]

      [37] Van Heerden F R, Huyser J J, Bradley D, Williams G, Holzapfel C W. Tetrahedron Lett, 1998, 39: 5281

    38. [38]

      [38] Sandberg M, Sydnes L K. Tetrahedron Lett, 1998, 39: 6361

    39. [39]

      [39] Sanderson W R. EP Patent 125 781. 1984

    40. [40]

      [40] Shirini F, Mamaghani M, Mostashari-Rad T, Abedini M. Bull Korean Chem Soc, 2010, 31: 2399

    41. [41]

      [41] Karimi B, Seradj H, Ebrahimian G R. Synlett, 2000, 1: 623

    42. [42]

      [42] Manjula K, Pasha M A. Synth Commun, 2007, 37: 1563

    43. [43]

      [43] Desai U V, Thopta T S, Pore D M, Wadgaonkar P P. Catal Commun, 2006, 7: 508

    44. [44]

      [44] Wang M, Gong H, Jiang H, Wang Z C. Synth Commun, 2006, 36: 1953

    45. [45]

      [45] Aggarwal V K, Fonquerna S, Vennall G P. Synlett, 1998: 849

    46. [46]

      [46] Karimi B, Maleki J. J Org Chem, 2003, 68: 4951

    47. [47]

      [47] Negron G E, Palacios L N, Angeles D, Lomas L, Gavino R. J Braz Chem Soc, 2005, 16: 490

    48. [48]

      [48] Shirini F, Jolodar O G. J Mol Catal A, 2012, 356: 61

    49. [49]

      [49] Shirini F, Khaligh N G, Jolodar O G. J Iran Chem Soc, 2013, 10: 181

    50. [50]

      [50] Khaligh N G, Shirini F. Ultrason Sonochem, 2013, 20: 26

    51. [51]

      [51] Roeges N P G. A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures. New York: Wiley, 1994

    52. [52]

      [52] Philip D, Eapen A, Aruldhas G. J Solid State Chem, 1995, 116: 217

    53. [53]

      [53] Chackalackal S M, Stafford F E. J Am Chem Soc, 1966, 88: 4815

    54. [54]

      [54] Silverstein R M, Bassler G C, Morrill T C. Spectrometric Identification of Organic Compounds. New York: John Wiley and Sons, 1991

    55. [55]

      [55] Kemp W. Organic Spectroscopy. London: MacMillan, 1996

    56. [56]

      [56] Suwan J, Zhang Z, Li B, Vongchan P, Meepowpan P, Zhang F, Mousa S A, Mousa S, Premanode B, Kongtawelert P, Linhardt R J. Carbohydrate Res, 2009, 344: 1190

    57. [57]

      [57] Grzyb B, Machnikowski J, Weber J V. J Anal Appl Pyrol, 2004, 72: 121

    58. [58]

      [58] McCurdie M P, Belfiore L A. Polymer, 1999, 40: 2889

    59. [59]

      [59] Gill N S, Nuttall R H, Scaife D E, Sharp D W A. J Inorg Nucl Chem, 1961, 18: 79

    60. [60]

      [60] Williams W J. Handbook of Anion Determination. London: Butterworth, 1979. 416

    61. [61]

      [61] Villagran C, Deetlefs M, Pitner W R, Hardacre C. Anal Chem, 2004, 76: 2118

    62. [62]

      [62] Wu K H, Wang Y R, Hwu W H. Polym Degrad Stab, 2003, 79: 195

    63. [63]

      [63] Pardey A J, Rojas A D, Yánez J E, Betancourt P, Scott C, Chinea C, Urbina C, Moronta D, Longo C. Polyhedron, 2005, 24: 511

    64. [64]

      [64] Duan Z Y, Gu Y L, Zhang J, Zhu L Y, Deng Y Q. J Mol Catal A, 2006, 250: 163

    65. [65]

      [65] Xing H B, Wang T, Zhou Z H, Dai Y Y. J Mol Catal A, 2007, 264: 53

    66. [66]

      [66] Thomazeau C, Olivier-Bourbigou H, Magna L, Luts S, Gilbert B. J Am Chem Soc, 2003, 125: 5264

    67. [67]

      [67] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 695

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