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
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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] Smith K. Solid Supports and Catalysis in Organic Synthesis. New York: Ellis Horwood and PTR Prentice Hall, 1992
-
[2]
[2] Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513
-
[3]
[3] Turro N J. Tetrahedron, 1987, 43: 1589
-
[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] Chehardoli G, Zolfigol M A, Faal-Rastegar T, Mallakpour S, Ghorbani-Choghamaranid A. J Chem Sci, 2009, 121: 441
-
[6]
[6] Khaligh N G, Shirini F. J Mol Catal A, 2011, 348: 20
-
[7]
[7] Khaligh N G. Ultrason Sonochem, 2012, 19: 736
-
[8]
[8] Khaligh N G. Tetrahedron Lett, 2012, 53: 1637
-
[9]
[9] Cole-Hamilton D J. Science, 2003, 299: 1702
-
[10]
[10] Curzons A, Constable C C, Cunningham V L. Clean Prod Process, 1999, 1: 82
-
[11]
[11] Tanaka K. Solvent-Free Organic Synthesis. Weinheim: Wiley-VCH, GmbH and KGaA, 2004
-
[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] Shaabani A, Ghadari R, Rahmati A, Rezayan A H. J Iran Chem Soc, 2009, 6: 710
-
[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] Otera J. Esterification: Methods, Reactions and Applications. Weinheim: Wiley-VCH, 2003
-
[16]
[16] Sun X L, Kai T, Takayanagi H, Furuhata K. Synlett, 1999: 1399
-
[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] Scriven E F V. Chem Soc Rev, 1983, 12: 129
-
[19]
[19] Höfle G, Steglich V, Vorbrüggen H. Angew Chem Int Ed, 1978, 17: 569
-
[20]
[20] Cope A C, Herrich E C. Organic Synthesis Collective. Vol. IV. New York: Wiley, 1963. 304
-
[21]
[21] Li A X, Li T S, Ding T H. Chem Commun, 1997: 1389
-
[22]
[22] Hagiwara H, Morohashi K, Suzuki T, Ando M, Yamamoto I, Kato M. Synth Commun, 1998, 28: 2001
-
[23]
[23] Ballini R, Bosica G, Carloni S, Ciaralli L, Maggi R, Sartori G. Tetrahedron Lett, 1998, 39: 6049
-
[24]
[24] Niknam K, Saberi D. Appl Catal A, 2009, 366: 220
-
[25]
[25] Joseph J K, Jain S L, Sain B. J Mol Catal A, 2007, 267: 108
-
[26]
[26] Niknam K, Saberi D. Tetrahedron Lett, 2009, 50: 5210
-
[27]
[27] Shirini F, Zolfigol MA, Mohammadi K. Bull Korean Chem Soc, 2004, 25: 325
-
[28]
[28] Chakraborti A K, Gulhane R. Chem Commun, 2003: 1896
-
[29]
[29] Heravi M M, Behbahani F K, Bamoharram F F. J Mol Catal A, 2006, 253: 16
-
[30]
[30] Khaligh N G. J Mol Catal A, 2012, 363-364: 90
-
[31]
[31] Khaligh N G. RSC Adv, 2013, 3: 99
-
[32]
[32] Trost B M, Lee C B. J Am Chem Soc, 2001, 123: 3687
-
[33]
[33] Gregory M J. J Chem Soc B, 1970: 1201
-
[34]
[34] Sandberg M, Sydnes L K. Org Lett, 2000, 2: 687
-
[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] Freeman F, Karchefski E M. J Chem Eng Data, 1977, 22: 355
-
[37]
[37] Van Heerden F R, Huyser J J, Bradley D, Williams G, Holzapfel C W. Tetrahedron Lett, 1998, 39: 5281
-
[38]
[38] Sandberg M, Sydnes L K. Tetrahedron Lett, 1998, 39: 6361
-
[39]
[39] Sanderson W R. EP Patent 125 781. 1984
-
[40]
[40] Shirini F, Mamaghani M, Mostashari-Rad T, Abedini M. Bull Korean Chem Soc, 2010, 31: 2399
-
[41]
[41] Karimi B, Seradj H, Ebrahimian G R. Synlett, 2000, 1: 623
-
[42]
[42] Manjula K, Pasha M A. Synth Commun, 2007, 37: 1563
-
[43]
[43] Desai U V, Thopta T S, Pore D M, Wadgaonkar P P. Catal Commun, 2006, 7: 508
-
[44]
[44] Wang M, Gong H, Jiang H, Wang Z C. Synth Commun, 2006, 36: 1953
-
[45]
[45] Aggarwal V K, Fonquerna S, Vennall G P. Synlett, 1998: 849
-
[46]
[46] Karimi B, Maleki J. J Org Chem, 2003, 68: 4951
-
[47]
[47] Negron G E, Palacios L N, Angeles D, Lomas L, Gavino R. J Braz Chem Soc, 2005, 16: 490
-
[48]
[48] Shirini F, Jolodar O G. J Mol Catal A, 2012, 356: 61
-
[49]
[49] Shirini F, Khaligh N G, Jolodar O G. J Iran Chem Soc, 2013, 10: 181
-
[50]
[50] Khaligh N G, Shirini F. Ultrason Sonochem, 2013, 20: 26
-
[51]
[51] Roeges N P G. A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures. New York: Wiley, 1994
-
[52]
[52] Philip D, Eapen A, Aruldhas G. J Solid State Chem, 1995, 116: 217
-
[53]
[53] Chackalackal S M, Stafford F E. J Am Chem Soc, 1966, 88: 4815
-
[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] Kemp W. Organic Spectroscopy. London: MacMillan, 1996
-
[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] Grzyb B, Machnikowski J, Weber J V. J Anal Appl Pyrol, 2004, 72: 121
-
[58]
[58] McCurdie M P, Belfiore L A. Polymer, 1999, 40: 2889
-
[59]
[59] Gill N S, Nuttall R H, Scaife D E, Sharp D W A. J Inorg Nucl Chem, 1961, 18: 79
-
[60]
[60] Williams W J. Handbook of Anion Determination. London: Butterworth, 1979. 416
-
[61]
[61] Villagran C, Deetlefs M, Pitner W R, Hardacre C. Anal Chem, 2004, 76: 2118
-
[62]
[62] Wu K H, Wang Y R, Hwu W H. Polym Degrad Stab, 2003, 79: 195
-
[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] Duan Z Y, Gu Y L, Zhang J, Zhu L Y, Deng Y Q. J Mol Catal A, 2006, 250: 163
-
[65]
[65] Xing H B, Wang T, Zhou Z H, Dai Y Y. J Mol Catal A, 2007, 264: 53
-
[66]
[66] Thomazeau C, Olivier-Bourbigou H, Magna L, Luts S, Gilbert B. J Am Chem Soc, 2003, 125: 5264
-
[67]
[67] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 695
-
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