Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 5967-5974

  Chakraborti, Asit K ^a   Singh, Bavneet ^a   Chankeshwara, Sunay V ^a   Patel, Alpesh R ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ALUMINUM; AMINES; AMINO ACIDS; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; CONDENSATION; ESTERIFICATION; ESTERS; GELATION; INDUSTRIAL APPLICATIONS; INORGANIC ACIDS; ORGANIC ACIDS; SILICA; SILICA GEL;

ALIPHATIC ALCOHOL; ALIPHATIC CARBOXYLIC ACIDS; CATALYST SYSTEM; CATALYTIC EFFICIENCIES; CHEMICAL EQUATIONS; CHEMO-SELECTIVITY; CHIRAL ALCOHOLS; CHIRAL AMINO ACIDS; DEPROTECTION; DETRIMENTAL EFFECTS; EQUIMOLAR AMOUNT; ESTER FORMATION; HIGH YIELD; OPTICAL PURITY; PERCHLORIC ACIDS; PRODRUGS; PROPARGYL; PROTIC ACIDS; RECYCLABLE CATALYST; SOLID SUPPORTS;

SILICON COMPOUNDS;

ALCOHOL; ALLYL COMPOUND; CARBOXYLIC ACID DERIVATIVE; IBUPROFEN; PERCHLORIC ACID; SILICA GEL; ALCOHOL DERIVATIVE; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND; PERCHLORATE; SILICON DIOXIDE;

ACIDITY; ALKALINITY; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DEPROTECTION REACTION; ESTERIFICATION; IMMOBILIZATION; POLYMERIZATION; CHEMISTRY;

ALCOHOLS; CARBOXYLIC ACIDS; ESTERIFICATION; HETEROCYCLIC COMPOUNDS; PERCHLORATES; SILICA GEL; SILICON DIOXIDE;

EID: 70349155051     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900614s     Document Type: Article

References (64)

1. Otera, J. Esterification: Methods, Reactions and Applications; Wiley-VCH: Weinheim, Germany, 2003.
2. Greene, T. W.; Wuts, P. G. M. Protective Groups Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
3. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
4. Dugger, R. W.; Ragan, J. A.; Ripin, D. H. B. Org. Process Res. Dev. 2005, 9, 253.
5. Tundo, P.; Anastas, P.; Black, D. S.; Breen, J.; Collins, T.; Memoli, S.; Miyamoto, J.; Polyakoff, M.; Tumas, W. Pure Appl. Chem. 2000, 72, 1207.
6. Basak (née Nandi), A; Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett., 1998, 39, 4883 and the references cited therein.
7. Chakraborti, A. K.; Basak (née Nandi), A.; Grover, V. J. Org. Chem. 1999, 64, 8014 and the references cited therein.
8. Selva, M.; Perosa, A. Green Chem. 2008, 10, 457.
9. Tundo, P.; Selva, M. Acc. Chem. Res. 2002, 35, 706.
10. Selva, M.; Tundo, P. J. Org. Chem. 2006, 71, 1464.
11. Shieh, W.-C.; Dell, S.; Repič, O. J. Org. Chem. 2002, 67, 2188.
12. Shieh, W.-C.; Dell, S.; Repič, O. Tetrahedron Lett. 2002, 43, 5607.
13. (a) Trost, B. M. Science 1991, 254, 1471.
14. (b) Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259.
15. (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140.
16. (b) Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5249.
17. (c) Mantri, K.; Komura, K.; Sugi, Y. Green Chem. 2005, 7, 677.
18. (d) Bartoli, G.; Boeglin, J.; Bosco, M.; Locatelli, M.; Massaccesi, M.; Melchiorre, P.; Sambri, L. Adv. Synth. Catal. 2005, 347, 33 and references cited therein.
19. (e) Zhu, H.-P.; Yang, F.; Tang, J.; He, M.-Y. Green Chem. 2003, 5, 38.
20. (f) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C., Jr.; Davis, J. H. J. Am. Chem. Soc. 2002, 124, 5962.
21. (g) Gang, L.; Xinzong, L.; Eli, W. New J. Chem. 2007, 71, 348.
22. (h) Zhang, H.; Xu, F.; Zhou, X.; Zhang, G.; Wang, C. Green Chem. 2007, 9, 1208.
23. (a) Pittelkow, M.; Kamounah, F. S.; Boas, U.; Pedersen, B.; Christensen, J. B. Synthesis 2004, 2485.
24. (b) Held, I.; Hoff, P.; Stephenson, D. S.; Zipse, H. Adv. Synth. Catal. 2008, 350, 1891.
25. -1: Sweet, D. V. Registry of Toxic Effects of Chemical Substances, 1985-1986; U.S. Govt. Printing Office: Washington, D.C., 1988; p 3336.
26. Goossen, L.; Döhring, A. Adv. Synth. Catal. 2003, 345, 943.
27. Otera, J. Angew. Chem., Int. Ed. 2001, 40, 2044.
28. (a) Wilson, K.; Clark, J. H. Pure Appl. Chem. 2000, 72, 1313.
29. (b) Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199.
30. Ertl, G. Angew. Chem., Int. Ed. 2008, 47, 3524.
31. (a) Chakraborti, A. K.; Gulhane, R. J. Chem. Soc., Chem. Commun. 2003, 1896.
32. (b) Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44, 3521.
33. (c) Chakraborti, A. K.; Gulhane, R. Indian Patent, 266/DEL/2003 (10-13-2003).
34. (a) Kumar, R.; Kumar, D.; Chakraborti, A. K. Synthesis 2007, 299.
35. (b) Khatik, G. L.; Sharma, G.; Kumar, R.; Chakraborti, A. K. Tetrahedron 2007, 63, 1200.
36. (c) Rudrawar, S.; Besra, R. C.; Chakraborti, A. K. Synthesis 2006, 2767.
37. (d) Chakraborti, A. K.; Chankeshwara, S. V. Org. Biomol. Chem. 2006, 4, 2769.
38. (e) Sharma, G.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2008, 49, 4272.
39. (f) Kumar, D.; Kumar, R.; Chakraborti, A. K. Synthesis 2008, 1249.
40. 2: (a) Agarwal, A.; Rani, S.; Vankar, Y. D. J. Org. Chem. 2004, 6137.
41. (b) Misra, A. K.; Tiwari, P.; Madhusudan, S. K. Carbohydr. Res. 2005, 340, 325.
42. (c) Mukhopadhyay, B.; Russell, D. A.; Field, R. A. Carbohydr. Res. 2005, 340, 1075.
43. (d) Du, Y.; Wei, G.; Cheng, S.; Hua, Y.; Linhardt, R. J. Tetrahedron Lett. 2006, 47, 307.
44. (e) Maheswara, M.; Siddaiah, V.; Damu, G. L. V.; Rao, C. V. ARKIVOC 2006, 201.
45. (f) Khan, A. T.; Ghosh, S.; Choudhury, L. H. Eur. J. Org. Chem. 2006, 2226.
46. (g) Kamble, V. T.; Jamode, V. S.; Joshi, N. S.; Biradar, A. V.; Deshmukh, R. Y. Tetrahedron Lett. 2006, 47, 5573.
47. (h) Das, B.; Majhi, A.; Banerjee, J. Tetrahedron Lett. 2006, 47, 7619.
48. (i) Narasimhulu, M.; Reddy, T. S.; Mahesh, K. C.; Prabhakar, P.; Rao, Ch. B.; Venkateswarlu, Y. J. Mol. Catal. A: Chem 2007, 266, 114.
49. (j) Nagarapu, L.; Paparaju, V.; Pathuri, G.; Kantevari, S.; Pakkiru, R. R.; Kamalla, R. J. Mol. Catal. A: Chem. 2007, 267, 53.
50. (k) Bigdeli, M. A.; Nemati, F.; Mahdavinia, G. H. Tetrahedron Lett. 2007, 48, 6801.
51. (l) Colinas, P. A.; Bravo, R. D. Carbohydr. Res. 2007, 342, 2297.
52. (m) Naik, T. R. R.; Naik, H. S. B.; Raghavendra, M.; Bindu, P. J.; Mahadevan, K. M. J. Sulf. Chem. 2007, 28, 589.
53. (n) Nagarapu, L.; Aneesa; Peddiraju, R.; Apuri, S. Catal. Commun. 2007, 8, 1973.
54. (o) Meshram, H. M.; Reddy, P. N.; Murthy, P. V.; Yadav, J. S. Synth. Commun. 2007, 37, 4117.
55. (p) Shaterian, H. R.; Yarahmadi, H.; Ghashang, M. Tetrahedron 2008, 64, 1263.
56. (q) Heydari, A.; MaMani, L. Appl. Organomet. Chem. 2008, 22, 12.
57. (r) Gupta, R.; Gupta, M.; Paul, S.; Gupta, R.; Loupy, A. Lett. Org. Chem. 2008, 5, 153.
58. Chakraborti, A. K.; Chankeshwara, S. V.; Singh, B. Indian patent 2764/DEL/2007 (Dec 28, 2007).
59. (a) Bhagat, S.; Ph.D. Thesis, Aug 2008, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Punjab 160 062, India.
60. (b) Mukhopadhyay, B. Tetrahedron Lett. 2006, 47, 4337.
61. (c) Sheritan, H. R.; Khorami, F.; Amirzadeh, A.; Ghashang, M. Phosphorus Sulfur Relat. Elem. 2008, 183, 2865.
62. (a) Bansal, A. K.; Khar, R. K.; Dubey, R.; Sharma, A. K. Indian J. Exp. Biol. 2001, 39, 280.
63. (b) Bansal, A. K.; Khar, R. K.; Dubey, R.; Sharma, A. K. Pharmazie 1994, 49, 422.
64. Salomė, C.; Kohn, H. Tetrahedron 2009, 65, 456.