Indium tribromide as a highly efficient and versatile catalyst for chemoselective synthesis of acylals from aldehydes under solvent-free conditions

Synlett

Volumn , Issue 10, 2004, Pages 1727-1730

  Yin, Liang ^a   Zhang, Zhan Hui ^a   Wang, Yong Mei ^a   Pang, Mei Li ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Acylals; Aldehydes; Chemoselective; Indium tribromide; Solvent free conditions

Indexed keywords

ALDEHYDE DERIVATIVE; BROMINE DERIVATIVE; INDIUM TRIBROMIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; SYNTHESIS;

EID: 4143107977     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829549     Document Type: Article

References (88)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999, 306.
2. Gregory, M. J. J. Chem. Soc. B 1970, 1201.
3. (a) Li, T.-S.; Zhang, Z.-H.; Fu, C.-G. Tetrahedron Lett. 1997, 38, 3285.
4. (b) Ballini, R.; Bordoni, M.; Bosica, G.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1998, 39, 7587.
5. (c) Narayana, C.; Padmanabhan, S.; Kabalka, G. W. Tetrahedron Lett. 1990, 31, 6977.
6. (d) Cotelle, P.; Catteau, J.-P. Tetrahedron Lett. 1992, 33, 3855.
7. (e) Perez, E. R.; Marrero, A. L.; Perez, R.; Autie, M. A. Tetrahedron Lett. 1995, 36, 1779.
8. (f) Aggarwal, V. K.; Fonquerna, S.; Vernnall, G. P. Synlett 1998, 849.
9. (g) Zolfigol, M. A.; Zebarjadian, M. H.; Mohammadpoor-Baltork, I.; Shamsipur, M. Synth. Commun. 2002, 32, 2803.
10. (h) Jin, T.-S.; Ma, Y.-R.; Zhang, Z.-H.; Li, T.-S. Synth. Commun. 1997, 27, 3379.
11. (a) Sydnes, L. K.; Sandberg, M. Tetrahedron 1997, 55, 12679.
12. (b) Sandberg, M.; Sydnes, L. K. Tetrahedron Lett. 1998, 39, 6361.
13. (c) Sinder, B. B.; Amin, S. G. Synth. Commun. 1978, 8, 117.
14. (d) Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001, 123, 12191.
15. (e) Trost, B. M.; Lee, J. M.; Weiss, J. J. Am. Chem. Soc. 1995, 117, 7247.
16. (f) Yadav, J. S.; Reddy, B. V. S.; Reddy, G. S. K. K. Tetrahedron Lett. 2000, 41, 2695.
17. (g) Heerden, F. R.; Huyser, J. J.; Williams, D. B. G.; Holzapfer, C. W. Tetrahedron Lett. 1998, 39, 5281.
18. (h) Banks, R. E.; Miller, J. A.; Nunn, M. J.; Stanley, P.; Weakley, T. J. R.; Ullah, Z. J. Chem. Soc., Perkin Trans. 1 1981, 1096.
19. (i) Sandbery, M.; Sydnes, L. K. Org. Lett. 2000, 2, 687.
20. Frick, J. G.; Harper, R. J. J. Appl. Polym. Sci. 1984, 29, 1433.
21. (a) Angelis, Y. S.; Smonou, I. Tetrahedron Lett. 1997, 38, 8109.
22. (b) Angelis, Y. S.; Smonou, I. Tetrahedron Lett. 1998, 39, 2823.
23. 4: Tomita, M.; Kikuchi, T.; Bessho, K.; Hori, T.; Inubushi, Y. Chem. Pharm. Bull. 1963, 11, 1484.
24. 4: Davey, W.; Gwilt, J. R. J. Chem. Soc. 1957, 1008.
25. 3H: Freeman, F.; Karchefski, E. M. J. Chem. Eng. Data 1977, 22, 355.
26. 4: Marshall, J. A.; Wuts, P. G. M. J. Org. Chem. 1977, 42, 1794.
27. 2: Scriabire, I. Bull. Chem. Soc. Fr. 1961, 1194.
28. 3: Kochhar, K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyaksha, S. N.; Pinnick, H. W. J. Org. Chem. 1983, 48, 1765.
29. (c) See also: Li, Y.-Q. Chin. J. Org. Chem. 2003, 23, 686.
30. 4: Jin, T.-S.; Du, G.-Y.; Li, T.-S. Indian J. Chem., Sect. B 1998, 37, 939.
31. (e) LiBr: Kumar, H. M. S.; Reddy, B. V. S.; Reddy, P. T.; Yadav, J. S. J. Chem. Res., Synop. 2000, 86.
32. 3: Michie, J. K.; Miller, J. A. Synthesis 1981, 824.
33. 6: Karimi, B.; Ebrahiminan, G.-R.; Seradj, H. Synth. Commun. 2002, 32, 669.
34. 3: Yadav, J. S.; Reddy, B. V. S.; Srinivas, C. Synth. Commun. 2002, 32, 1175.
35. (i) CAN: Roy, S. C.; Banerjee, B. Synlett 2002, 1677.
36. 4: Yadav, J. S.; Reddy, B. V. S.; Venugopal, C.; Ramalingam, T. Synlett 2002, 604.
37. 2: Ranu, B. C.; Dutta, J.; Das, A. Chem. Lett. 2003, 32, 366.
38. 2O: Zhang, X.; Li, L.; Zhang, G. Green Chem. 2003, 5, 646.
39. 4: Smitha, G.; Reddy, C. S. Tetrahedron 2003, 59, 9571.
40. 2O: Chakraborti, A. K.; Thilagavathi, R.; Kumar, R. Synthesis 2004, 831.
41. 2O: Aggen, D. H.; Arnold, J. N.; Hayes, P. D.; Smoter, N. J.; Mohan, R. S. Tetrahedron 2004, 60, 3675.
42. 2O: Romanelli, G. P.; Thomas, H. J.; Baronetti, G. T.; Autino, J. C. Tetrahedron Lett. 2003, 44, 1301.
43. 40: Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.; Amani, K. Tetrahedron Lett. 2003, 44, 3951.
44. (a) Nafion-H: Olah, G. A.; Mehrotra, A. K. Synthesis 1982, 962.
45. (b) Expansive graphite: Jin, T.-S.; Du, G.-Y.; Zhang, Z.-H.; Li, T.-S. Synth. Commun. 1997, 27, 2261.
46. (c) Zeolite Y: Ballini, R.; Bordoni, M.; Bosica, G.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1998, 39, 7587.
47. (d) Y-Zeolite: Pereira, C.; Gigante, B.; Marcelo-Curto, M. J.; Carreyre, H.; Pérot, G.; Guisnet, M. Synthesis 1995, 1077.
48. (e) β-Zeolite: Kumar, P.; Hegde, V. R.; Kumar, T. P. Tetrahedron Lett. 1995, 36, 601.
49. (f) Envirocat EPZG®: Bandgar, B. P.; Mahajan, N. P.; Mulay, D. P.; Thote, J. L.; Wadgaonkar, P. P. J. Chem. Res., Synop. 1995, 470.
50. (g) Montmorillonite K-10: Zhang, Z.-H.; Li, T.-S.; Fu, C.-G. J. Chem. Res., Synop. 1997, 174.
51. 3+-montmorillonite: Li, T.-S.; Zhang, Z.-H.; Gao, Y.-J. Synth. Commun. 1998, 25, 4665.
52. (i) metal cation-exchanged montmorillonite: Jankovic, L.; Komadel, P. J. Catal. 2003, 278, 227.
53. (j) Zn-montmorillonite: Nagy, N. M.; Jakab, M. A.; Konya, J.; Antus, S. Appl. Clay Sci. 2002, 27, 23.
54. (k) HZSM-5: Joshi, M. V.; Narasimhan, C. S.; Mukesh, D. Zeolites 1995, 15, 597.
55. 2: Li, Y.-Q.; Cheng, L.-H. Chin. Chem. Lett. 2001, 12, 565.
56. 3: Li, Y.-Q. Synth. Commun. 2000, 30, 3913.
57. (n) Sulfated zirconia: Raju, S. V. N. J. Chem. Res., Synop. 1996, 68.
58. 2-: Jin, T.-S.; Ma, Y.-R.; Sun, X.; Liang, D.; Li, T.-S. J. Chem. Res., Synop. 2000, 96.
59. 2: Jin, T.-S.; Feng, G.-L.; Yang, M.-N.; Li, T.-S. Synth. Commun. 2004, 34, 1645.
60. Deka, N.; Kalita, D. J.; Borah, R.; Sarma, J. C. J. Org. Chem. 1997, 62, 1563.
61. Karimi, B.; Seradj, H.; Ebrahimian, G. R. Synlett 2000, 623.
62. Deka, N.; Borah, R.; Kalita, D. J.; Sarma, J. C. J. Chem. Res., Synop. 1998, 94.
63. 2: Chandra, K. L.; Saravanan, P.; Singh, V. K. Synlett 2000, 359.
64. 3: Aggarwal, V. K.; Fonquerna, S.; Vennall, G. P. Synlett 1998, 849.
65. (c) LiOTf: Karimi, B.; Maleki, J. J. Org. Chem. 2003, 68, 4951.
66. Li, C.-J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
67. (a) Loh, T.-P.; Pei, J.; Cao, G.-Q. Chem. Commun. 1996, 1819.
68. (b) Loh, T.-P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315.
69. (c) Kobayashi, S.; Busujima, T.; Nagayama, S. Tetrahedron Lett. 1998, 59, 1579.
70. (d) Loh, T.-P.; Wei, L.-L. Tetrahedron Lett. 1998, 39, 323.
71. (e) Loh, T.-P.; Wei, L.-L. Synlett 1998, 975.
72. (f) Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736.
73. (g) Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 369.
74. (h) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347.
75. (i) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
76. (j) Babu, G.; Perumal, P. T. Aldrichimica Acta 2000, 33, 16.
77. (k) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015.
78. (a) Ceschi, M. A.; de Araujo Felix, L.; Peppe, C. Tetrahedron Lett. 2000, 41, 9695.
79. (b) Fu, N.-Y.; Yuan, Y.-H.; Cao, Z.; Wang, S.-W.; Wang, J.-T.; Peppe, C. Tetrahedron 2002, 58, 4801.
80. (c) Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Swamy, T. Tetrahedron Lett. 2003, 44, 6055.
81. (d) Yadav, J. S.; Reddy, B. V. S.; Raju, A. K.; Rao, C. V. Tetrahedron Lett. 2002, 43, 5437.
82. (e) Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Selva, S.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 3700.
83. (f) Agnusdei, M.; Bandini, M.; Melloni, A.; Umani-Ronchi, A. J. Org. Chem. 2003, 68, 7126.
84. (g) Yadav, J. S.; Reddy, B. V. S.; Gakul, B. Green Chem. 2003, 5, 264.
85. (h) Yadav, J. S.; Reddy, B. V. S. Synthesis 2002, 511.
86. (i) Yadav, J. S.; Reddy, B. V. S.; Parimala, G. Synlett 2002, 1143.
87. (j) Yadav, J. S.; Reddy, B. V. S.; Baishya, G. Synlett 2003, 396.
88. (k) Yadav, J. S.; Reddy, B. V. S.; Swamy, T. Synthesis 2004, 106.