Introduction of N-sulfonic acid poly(4-vinylpyridinum) chloride as an efficient and reusable catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes

Journal of Molecular Catalysis A: Chemical

Volumn 356, Issue , 2012, Pages 61-69

  Shirini, Farhad ^a   Jolodar, Omid Goli ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

1,1 Diacetates; N sulfonic poly(4 vinylpyridinium) chloride; Poly(4 vinylpyridine); Solid acids; Solvent free reaction conditions

Indexed keywords

1 ,1-DIACETATES; N-SULFONIC POLY(4-VINYLPYRIDINIUM) CHLORIDE; POLY(4-VINYLPYRIDINE); SOLID ACIDS; SOLVENT FREE REACTION;

ALDEHYDES; CHLORINE COMPOUNDS; METHANOL;

CATALYSTS;

EID: 84857366621     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2012.01.002     Document Type: Article

References (84)

1. D. Choudhary, S. Paul, R. Gupta, and J.H. Clark Green Chem. 8 2006 479 482
2. A. Ghorbani-Choghamarani, and S. Sardari J. Sulfur. Chem. 32 2011 63 69
3. R. Dalpozzo, G. Bartoli, L. Sambri, and P. Melchiorre Chem. Rev. 110 2010 3501 3551
4. A.K. Chakraborti, B. Singh, S.V. Chankeshwara, and A.R. Patel J. Org. Chem. 74 2009 5967 5974
5. G. Sharma, R. Kumar, and K.C. Asit Tetrahedron Lett. 49 2008 4272 4275
6. R. Kumar, D. Kumar, and K.C. Asit Synthesis 2007 299 303
7. K. Tanabe, and W.F. Hölderich Appl. Catal. A 181 1999 399 434
8. D.J. Cole-Hamilton Science 299 2003 1702 1706
9. A. Chakrabarti, and M.M. Sharma React. Polym. 20 1993 1 45
10. J.M. Riego, Z. Sedin, J.M. Zaldivar, N.C. Marziano, and C. Tortato Tetrahedron Lett. 37 1996 513 516
11. N.J. Turro Tetrahedron 43 1987 1589 1616
12. M.A. Zolfigol, G. Chehardoli, M. Dehghanian, K. Niknam, F. Shirini, and A. Khoramabadi-Zad J. Chin. Chem. Soc. 55 2008 885 889
13. G. Chehardoli, M.A. Zolfigol, T. Faal-Rastegar, S. Mallakpour, and A. Ghorbani-Choghamaranid J. Chem. Sci. 121 2009 441 447
14. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley and Sons New York pp. 306-307
15. M.J. Gregory J. Chem. Soc. B 1970 1201 1207
16. F.R. Heerden, J.J. Huyser, D.B.G. Williams, and C.W. Holzapfer Tetrahedron Lett. 39 1998 5281 5284
17. B.M. Trost, and C. Lee J. Am. Chem. Soc. 123 2001 12191 12201
18. M. Sandberg, and L.K. Sydnes Tetrahedron Lett. 39 1998 6361 6364
19. K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Rajadhyaksha, and H.W. Pinnick J. Org. Chem. 48 1983 1765 1767
20. M. Tomita, T. Kikuchi, K. Bessho, T. Hori, and Y. Inubushi Chem. Pharm. Bull. 11 1963 1484 1490
21. R. Wegscheider, and E. Spath Monatsh. Chem. 30 1909 825 869
22. W. Davey, and J.R. Gwilt J. Chem. Soc. 1957 1008 1014
23. F. Freeman, and E.M. Karchetski J. Chem. Eng. Data 22 1977 355 357
24. J.A. Marshall, and P.G.M. Wuts J. Org. Chem. 42 1977 1794 1798
25. G.A. Olah, and A.K. Mehrotra Synthesis 1982 962 967
26. T.S. Jin, G.Y. Du, Z.H. Zhang, and T.S. Li Synth. Commun. 27 1997 2261 2262
27. T.S. Li, Z.H. Zhang, and C.G. Fu Tetrahedron Lett. 38 1997 3285 3288
28. B.M. Reddy, P.M. Sreekanth, and A. Kahn Synth. Commun. 34 2004 1839 1845
29. N. Deka, D.J. Kalita, R. Borah, and J.C. Sarma J. Org. Chem. 62 1997 1563 1564
30. J.M. Thomas Angew. Chem. Int. Ed. Engl. 27 1998 1673 1691
31. N. Daka, R. Borah, D.J. Kalita, and J.C. Sarma J. Chem. Res. 1998 94 95
32. I. Scriabire Bull. Soc. Chim. Fr. 1961 1194 1198
33. B.M. Trost, C.B. Lee, and J.M. Weiss J. Am. Chem. Soc. 117 1995 7247 7248
34. C.D. Wang, and M.H. Li Synth. Commun. 32 2002 3469 3473
35. T.S. Jin, G.Y. Du, and T.S. Li Indian J. Chem. B 37 1998 939 940
36. X.Y. Zhang, L.J. Li, and G.S. Zhang Green Chem. 5 2003 546 548
37. J.K. Michie, and J.A. Miller Synthesis 1981 824 825
38. J.S. Yadav, B.V.S. Reddy, and C. Srinivas Synth. Commun. 32 2002 1175 1180
39. L. Yin, Z.-H. Zhang, Y.-M. Wang, and M.-L. Pang Synlett 2004 1727 1730
40. B.F. Mirjalili, M.A. Zolfigol, A. Bamoniric, and N. Sheikhan J. Chin. Chem. Soc. 53 2006 955 959
41. M.M. Heravi, K. Bakhtiari, T. Benmorad, and H.A. Oskooie J. Chin. Chem. Soc. 54 2007 273 275
42. B.P. Bandgar, N.S. Joshi, and V.T. Kamble J. Chin. Chem. Soc. 54 2007 489 492
43. V.K. Aggarwal, S. Fonquerna, and G.P. Vennall Synlett 1998 849 852
44. K.L. Chandra, P. Saravanan, and V.K. Singh Synlett 2000 359 360
45. M.D. Carrigan, K.J. Eash, M.C. Oswald, and R.S. Mohan Tetrahedron Lett. 42 2001 8133 8135
46. B. Karimi, and J. Maleki J. Org. Chem. 68 2003 4951 4954
47. R. Ghosh, S. Maiti, A. Chakraborty, and R. Halder J. Mol. Catal. A: Chem. 215 2004 49 53
48. M.V. Joshi, and C.S. Narasimhan J. Catal. 141 1993 308 310
49. D. Karmakar, D. Prajapati, and J.S. Sandhu J. Chem. Res. 1998 382 383
50. Z.H. Zhang, T.S. Li, and C.G. Fu J. Chem. Res. 1997 174 175
51. T.S. Li, Z.H. Zhang, and Y.J. Gao Synth. Commun. 28 1998 4665 4671
52. T.S. Jin, Y.R. Ma, Z.H. Zhang, and T.S. Li Synth. Commun. 27 1997 3379 3383
53. P. Kumar, V.R. Hedge, and T.P. Kumar Tetrahedron Lett. 1995 601 602
54. C. Pereira, B. Gigante, M.J. Marcelocurto, H. Carreyre, G. Perot, and M. Guisnet Synthesis 1995 1077 1078
55. R. Ballini, M. Bordoni, G. Bosica, R. Maggi, and G. Sartori Tetrahedron Lett. 39 1998 7587 7590
56. B. Karimi, H. Seradj, and G.R. Ebrahimian Synlett 2000 623 624
57. S.C. Roy, and B. Banerjee Synlett 2002 1677 1678
58. T.S. Jin, G. Sun, Y.W. Li, and T.S. Li Green Chem. 4 2002 255 256
59. B. Karimi, G.R. Ebrahimian, and H. Seradj Synth. Commun. 32 2002 669 673
60. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, and K. Amani Tetrahedron Lett. 44 2003 3951 3954
61. G.P. Romanelli, H.J. Thomas, G.T. Baronetti, and J.C. Autino Tetrahedron Lett. 44 2003 1301 1303
62. M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, and M. Nocchetti Tetrahedron Lett. 43 2002 2709 2711
63. G. Smitha, and C.S. Reddy Tetrahedron 59 2003 9571 9576
64. N. Sumida, K. Nishioka, and T. Sato Synlett 2001 1921 1922
65. J.S. Yadav, B.V.S. Reddy, C. Venugopal, and T. Ramalingam Synlett 2002 604 606
66. H.M.S. Kumar, B.V.S. Reddy, P.T. Reddy, and J.S. Yadav J. Chem. Res. 2000 86 87
67. B.C. Rana, J. Dutta, and A. Das Chem. Lett. 2003 366 367
68. A.K. Chakraborti, R. Thilagavathi, and R. Kumar Synthesis 2004 831 833
69. D.H. Aggen, J.N. Arnold, P.D. Hayes, N.J. Smoter, and R.S. Mohan Tetrahedron Lett. 60 2004 3675 3679
70. A. Ziyaei, N. Azizi, and M.R. Saidi J. Mol. Catal. A: Chem. 238 2005 138 141
71. G.E. Negron, L.N. Palacios, D. Angeles, L. Lomas, R. Gavino, and J. Braz Chem. Soc. 16 3A 2005 490 494
72. B. Grzyb, J. Machnikowski, and J.V. Weber J. Anal. Appl. Pyrolysis 72 2004 121 130
73. M.P. McCurdie, and L.A. Belfiore Polymer 40 1999 2889 2902
74. L.N. Karklin, M.W. Kluev, and A.D. Pomogailo Kin. Kat. 24 1983 408 410
75. N.S. Gill, R.H. Nuttall, D.E. Scaife, and D.W.A. Sharp J. Inorg. Chem. 18 1961 79 87
76. N.P.G. Roeges A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures 1994 Wiley New York
77. D. Philip, A. Eapen, and G. Aruldhas J. Solid State Chem. 116 1995 217 223
78. S.M. Chackalackal, and F.E. Stafford J. Am. Chem. Soc. 88 21 1966 4815 4819
79. Y.X. Jiang, X.M. Chen, Y.F. Mo, and Z.F. Tong J. Mol. Catal. A: Chem. 213 2004 231 234
80. P. Salehi, M.A. Zolfigol, F. Shirini, and M. Baghbanzadeh Curr. Org. Chem. 10 2006 2171 2181
81. F. Shirini, M.A. Zolfigol, P. Salehi, and M. Abedini Curr. Org. Chem. 12 2008 183 202
82. E. Kolvari, A. Ghorbani-Choghamarani, P. Salehi, F. Shirini, and M.A. Zolfigol J. Iran. Chem. Soc. 2 2007 126 174
83. F. Shirini, M. Mamaghani, and S.V. Atghia Catal. Commun. 12 2011 1088 1094
84. N. Ghaffari Khaligh, and F. Shirini J. Mol. Catal. A: Chem. 348 2011 20 29