Preparation of highly active triflic acid functionalized SBA-15 catalysts for the synthesis of coumarin under solvent-free conditions

ChemCatChem

Volumn 8, Issue 2, 2016, Pages 336-344

  Kalita, Pranjal ^a,b   Baskar, Arun V ^c   Choy, Jin Ho ^c,d   Lakhi, Kripal S ^c,e   El Newehy, Mohamed ^f   Lawrence, Geoffrey ^c   Al Deyab, Salem S ^f   Balasubramanian, Veerappan V ^a   Vinu, Ajayan ^a,c,e  

^a NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^b THE ENERGY AND RESOURCES INSTITUTE   (India)

^c UNIVERSITY OF QUEENSLAND   (Australia)

^d Ewha Womans University   (South Korea)

^e UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

^f KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

acid catalysis; coumarins; mesoporous materials; nanoporous materials; SBA 15

Indexed keywords

CATALYSTS; CHARACTERIZATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GAS ADSORPTION; POROUS MATERIALS; SYNTHESIS (CHEMICAL); TEMPERATURE PROGRAMMED DESORPTION; X RAY DIFFRACTION;

ACID CATALYSIS; CATALYTIC EFFICIENCIES; COUMARINS; NANO-POROUS MATERIALS; NITROGEN ADSORPTION ISOTHERM; POWDER X RAY DIFFRACTION; SBA-15; SOLVENT FREE CONDITIONS;

MESOPOROUS MATERIALS;

EID: 84956593749     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201500884     Document Type: Article

References (66)

1. R. D. H. Murray, Prog. Chem. Org. Nat. Prod. 1991, 58, 84-316.
2. R. O'Kennedy, R. D. Thornes, Coumarins: Biology, Applications and Mode of Action, Wiley, Chichester, 1997;
3. L. A. Singer, N. P. Long, J. Am. Chem. Soc. 1966, 88, 5213-5219;
4. M. Zahradnik, The Production and Application of Fluorescent Brightening Agents, Wiley, New York, 1992.
5. R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, Occurrence, Chemistry and Biochemistry, Wiley, New York, 1982.
6. H. G. Raj, S. Gupta, G. Biswas, S. Singh, A. Singh, A. Jha, K. S. Bisht, S. K. Sharma, S. C. Jain, V. S. Parmar, Bioorg. Med. Chem. 1996, 4, 2225-2228;
7. J. M. Timonen, R. M. Nieminen, O. Sareila, A. Goulas, L. J. Moilanen, M. Haukka, P. Vainiotalo, E. Moilanen, P. H. Aulaskari, Eur. J. Med. Chem. 2011, 46, 3845-3850;
8. I. Kostova, S. Raleva, P. Genova, R. Argirova, Bioinorg. Chem. Appl. 2006, 1-9.
9. H. Von Pechmann, C. Duisberg, Chem. Ber. 1884, 17, 929-936.
10. J. R. Johnson, Org. React. 1942, 1, 210-265.
11. G. Jones, Org. React. 1967, 15, 204-599;
12. G. Brufola, F. Fringuelli, O. Piermatti, F. Pizzo, Heterocycles 1996, 43, 1257-1266.
13. R. L. Shirner, Org. React. 1942, 1, 1-37.
14. I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391-2430.
15. E. C. Horning, Organic Synthesis Coll., Vol. III, Wiley, New York, 1955, p. 281;
16. B. M. Reddy, B. Thirupathi, M. K. Patil, Open Catal. J. 2009, 2, 33-39.
17. P. K. Mandal, A. K. Misra, Lett. Org. Chem. 2006, 3, 848-853.
18. H. Appel, J. Chem. Soc. 1935, 1031-1032;
19. L. L. Woods, J. Sapp, J. Org. Chem. 1962, 27, 3703-3705;
20. Z. S. Ahmad, R. D. Desai, Proc. Ind. Acad. Sci. 5 A 1937, 227;
21. Z. S. Ahmad, R. D. Desai, Chem. Abstr. 1937, 31, 5785;
22. R. Robinson, F. Weygand, J. Chem. Soc. 1941, 386-391.
23. R. Hinze, M. C. Laufer, W. F. Holderich, W. Bonrath, T. Netscher, Catal. Today 2009, 140, 105-111;
24. D. A. Chaudhari, Chem. Ind. 1983, 568-575.
25. E. A. Gunnewegh, A. J. Hoefnagel, H. van Bekkum, J. Mol. Catal. A 1995, 100, 87-92.
26. A. de La Hoz, A. Moreno, E. Vazquez, Synth. Lett. 1999, 608-610.
27. S. Frère, V. Thiéry, T. Besson, Tetrahedron Lett. 2001, 42, 2791-2795;
28. T. Li, Z. Zhang, F. Yang, C. Fu, J. Chem. Res. 1998, 38-39.
29. M. K. Potdar, M. S. Rasalkar, S. S. Mohile, M. M. Salunkhe, J. Mol. Catal. A 2005, 235, 249-252;
30. Y. Gu, J. Zhang, Z. Duan, Y. Deng, Adv. Synth. Catal. 2005, 347, 512-516.
31. A. Sinhamahapatra, N. Sutradhar, B. Roy, P. Pal, H. C. Bajaj, A. B. Panda, Appl. Catal. B 2011, 103, 378-387.
32. K. Niknam, D. Saberi, M. Baghernejad, Chin. Chem. Lett. 2009, 20, 1444-1448.
33. B. Karimi, D. Zareyee, Org. Lett. 2008, 10, 3989-3992.
34. S. Selvakumar, M. Chidambaram, A. P. Singh, Catal. Commun. 2007, 8, 777-783.
35. P. Kalita, B. Sathyaseelan, A. Mano, S. M. J. Zaidi, M. A. Chari, A. Vinu, Chem. Eur. J. 2010, 16, 2843-2851.
36. P. Kalita, R. Kumar, Microporous Mesoporous Mater. 2012, 149, 1-9.
37. P. Kalita, R. Kumar, Microporous Mesoporous Mater. 2012, 164, 232-238.
38. D. O. Bennardi, G. P. Romanelli, J. C. Autino, L. R. Pizzio, Catal. Commun. 2009, 10, 576-581.
39. P. Kalita, R. Kumar, Appl. Catal. A 2011, 397, 250-258.
40. M. Nandi, J. Mondal, K. Sarkar, Y. Yamauchi, A. Bhaumik, Chem. Commun. 2011, 47, 6677-6679.
41. F. Shang, J. Sun, S. Wu, Y. Yang, Q. Kan, J. Guan, Microporous Mesoporous Mater. 2010, 134, 44-50.
42. Y.-C. Pan, H.-Y. Wu, L.-P. Lee, G.-L. Jheng, G. T. K. Fey, H.-M. Kao, Microporous Mesoporous Mater. 2009, 123, 78-85.
43. M. Chidambaram, D. Curulla-Ferre, A. P. Singh, B. G. Anderson, J. Catal. 2003, 220, 442-456.
44. D. O. Bennardi, G. P. Romanelli, J. C. Autino, L. R. Pizzio, Appl. Catal. A 2007, 324, 62-68.
45. J. A. Melero, R. Van Grieken, G. Morales, Chem. Rev. 2006, 106, 3790-3812;
46. M. A. Jackson, I. K. Mbraka, B. H. Shanks, Appl. Catal. A 2006, 310, 48-53;
47. Y. Gu, A. Karam, F. Jerome, J. Barrault, Org. Lett. 2007, 9, 3145-3148.
48. D. Zhao, Q. Huo, J. Feng, B. F. Chmelka, G. D. Stucky, J. Am. Chem. Soc. 1998, 120, 6024-6036;
49. P. Yang, D. Zhao, D. Margolese, B. F. Chmelka, G. D. Stucky, Nature 1998, 396, 152-155;
50. P. Yang, D. Zhao, D. Margolese, B. F. Chmelka, G. D. Stucky, Chem. Mater. 1999, 11, 2813-2826.
51. J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. T. Schmitt, C. T. Chen, D. H. Olson, E. W. Sheppard, S. B. McCullen, J. B. Higgins, J. L. Schlenker, J. Am. Chem. Soc. 1992, 114, 10834-10843.
52. A. Vinu, G. S. Kumar, K. Ariga, V. Murugesan, J. Mol. Catal. A 2005, 235, 57-66;
53. A. Vinu, B. M. Devassy, S. B. Halligudi, W. Bohlmannc, M. Hartmann, Appl. Catal. A 2005, 281, 207-213;
54. A. Vinu, J. Justus, C. Anand, D. P. Sawant, K. Ariga, T. Mori, P. Srinivasu, V. V. Balasubramanian, S. Velmathi, S. Alam, Microporous Mesoporous Mater. 2008, 116, 108-115.
55. M. Hartmann, A. Vinu, Langmuir 2002, 18, 8010-8016.
56. G. Herzberg, Infrared and Raman Spectra of Polyatomic Molecules, Van Nostrand, New York, 1945, p. 285.
57. L. J. Bellamy, The Infrared Spectra of Complex Molecules, Wiley, New York, 1960, p. 328.
58. C. J. Pouchert, The Aldrich Library of IR Spectra, Aldrich Chem. Co Library, 3rd ed., 1981, p. 533.
59. R. D. Howells, J. D. McCown, Chem. Rev. 1977, 77, 69-92.
60. A. N. Pârvulescu, B. C. Gagea, M. Alifanti, V. Pârvulescu, V. I. Parvulescu, S. Nae, A. Razus, G. Poncelet, P. Grange, J. Catal. 2001, 202, 319-323.
61. N. C. Marziano, L. D. Ronchin, C. Tortato, A. Zingales, A. A. Sheikh-Osman, J. Mol. Catal. A 2001, 174, 265-277.
62. D.-Q. Zhou, J.-H. Yang, G.-M. Dong, M.-Y. Huang, Y.-Y. Jiang, J. Mol. Catal. A 2000, 159, 85-87.
63. A. Vinu, P. Kalita, V. V. Balasubramanian, H. Oveisi, T. Selvan, A. Mano, M. A. Chari, B. V. S. Reddy, Tetrahedron Lett. 2009, 50, 7132-7136;
64. R. Chakravarti, P. Kalita, S. T. Selvan, H. Oveisi, V. V. Balasubramanian, M. L. Kantam, A. Vinu, Green Chem. 2010, 12, 49-53;
65. R. Chakravarti, H. Oveisi, P. Kalita, R. R. Pal, S. B. Halligudi, M. L. Kantam, A. Vinu, Microporous Mesoporous Mater. 2009, 123, 338-344;
66. P. Srinivasu, S. Alam, V. V. Balasubramanian, S. Velmathi, D. P. Sawant, W. Bohlmann, S. P. Mirajkar, K. Ariga, S. B. Halligudi, A. Vinu, Adv. Funct. Mater. 2008, 18, 640-651.