Phosphonic acid functionalized ordered mesoporous material: A new and ecofriendly catalyst for one-pot multicomponent biginelli reaction under solvent-free conditions

ACS Applied Materials and Interfaces

Volumn 6, Issue 2, 2014, Pages 933-941

  Pramanik, Malay ^a   Bhaumik, Asim ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

biphenyl bridged phosphonic acid; multicomponent reaction; ordered mesoporous material; organocatalyst; solvent free conditions

Indexed keywords

MULTI-COMPONENT REACTIONS; ORDERED MESOPOROUS MATERIALS; ORGANOCATALYSTS; PHOSPHONIC ACIDS; SOLVENT FREE CONDITIONS;

CATALYSTS; CHAINS; CONDENSATION REACTIONS; HYBRID MATERIALS; MAGIC ANGLE SPINNING; ORGANIC ACIDS; SOLVENTS; STRENGTH OF MATERIALS; SURFACES; TRANSMISSION ELECTRON MICROSCOPY; TWO DIMENSIONAL; X RAY DIFFRACTION;

MESOPOROUS MATERIALS;

CETRIMIDE; ORGANOSILICON DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHOROUS ACID; SILICON; SURFACTANT;

ADSORPTION; ARTICLE; CATALYSIS; CHEMISTRY; INFRARED SPECTROSCOPY; POROSITY; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

ADSORPTION; CATALYSIS; CETRIMONIUM COMPOUNDS; MICROSCOPY, ELECTRON, TRANSMISSION; ORGANOSILICON COMPOUNDS; PHOSPHOROUS ACIDS; POROSITY; SILICON; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE-ACTIVE AGENTS; X-RAY DIFFRACTION;

EID: 84892928721     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am404298a     Document Type: Article

References (63)

1. Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634
2. Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825-7827
3. Cala, L.; Mendoza, A.; Fananas, F. J.; RodrIguez, F. Chem. Commun. 2013, 49, 2715-2717
4. Yu, S.; You, X.; Liu, Y. Chem.-Eur. J. 2012, 18, 13936-13940
5. Huang, Y.; Yang, F.; Zhu, C. J. Am. Chem. Soc. 2005, 127, 16386-16387
6. Cohen, F.; Overman, L. E. J. Am. Chem. Soc. 2006, 128, 2594-2603
7. Li, N.; Chen, X. H.; Song, J.; Luo, S. W.; Fan, W.; Gong, L. Z. J. Am. Chem. Soc. 2009, 131, 15301-15310
8. Jain, S. L.; Singhal, S.; Sain, B. Green Chem. 2007, 9, 740-741
9. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; Reilly, B. C. O. J. Med. Chem. 1991, 34, 806-811
10. YarIm, M.; Sarac, S.; Ertan, M.; Batu, O.; Erol, K., II. Farmaco 1999, 54, 359-363
11. Sarac, S.; Yarim, M.; Ertan, M.; Boydag, S.; Erol, K. Pharmazie 1998, 53, 91-94
12. Barrow, J. C.; Nantermet, P. G.; Selnick, H. G.; Glass, K. L.; Rittle, K. E.; Gilbert, K. F.; Steele, T. G.; Homnick, C. F.; Freidinger, R. M.; Ransom, R. W.; Kling, P.; Reiss, D.; Broten, T. P.; Schorn, T. W.; Chang, R. S.; O'Malley, S. S.; Olah, T. V.; Ellis, J. D.; Barrish, A.; Kassahun, K.; Leppert, P.; Nagarathnam, D.; Forray, C. J. Med. Chem. 2000, 43, 2703-2718 and 61, 1153-1162
13. Tawfik, H. A.; Bassyouni, F.; Gamal-Eldeen, A. M.; Abo-Zeid, M. A.; El-Hamouly, W. S. Pharmacol. Rep. 2009.
14. Tu, S.; Zhu, X.; Shi, F.; Zhang, J.; Zhang, Y. J. Heterocycl. Chem. 2007, 44, 837-842
15. Sachdeva, H.; Saroj, R.; Khaturia, S.; Singh, H. L. J. Chil. Chem. Soc. 2012, 57, 1012-1016
16. Wang, Y.; Yang, H.; Yu, J.; Miao, Z.; Chena, R. Adv. Synth. Catal. 2009, 351, 3057-3062
17. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270-6272
18. Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111-9113
19. Hankari, S. E.; Motos-Perez, B.; Hesemann, P.; Bouhaouss, A.; Moreau, J. J. E. Chem. Commun. 2011, 47, 6704-6706
20. Prosa, N.; Turgis, R.; Piccardi, R.; Scherrmann, M. C. Eur. J. Org. Chem. 2012, 2188-2200
21. Sharma, S. D.; Gogoi, P.; Konwar, D. Green Chem. 2007, 9, 153-157
22. Gholap, A. R.; Venkatesan, K.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Green Chem. 2004, 6, 147-150
23. Weiss, C. J.; Marks, T. J. Dalton Trans. 2010, 39, 6576-6588
24. Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Nickias, P. N.; Marks, T. J. Angew. Chem., Int. Ed. 2000, 39, 1312-1316
25. Bellis, E.; Kokotos, G. J. Mol. Catal., A: Chem. 2005, 241, 166-174
26. Aguirre, M. R.; Saenz, L. D. L. T.; Flores, W. A.; Sanchez, A. R.; Elguezabal, A. A. Catal. Today 2005, 107, 310-314
27. Kim, H. S.; Song, Y. M.; Choi, J. S.; Yang, J. W.; Han, H. Tetrahedron 2004, 60, 12051-12057
28. Pereza, B. M.; Roeserb, J.; Thomasb, A.; Hesemanna, P. Appl. Organomet. Chem. 2013, 27, 290-299
29. Merino, E.; Sesto, E. V.; Maya, E. M.; Iglesias, M.; Sanchez, F.; Corma, A. Chem. Mater. 2013, 25, 981-988
30. Comotti, A.; Bracco, S.; Valsesia, P.; Ferretti, L.; Sozzani, P. J. Am. Chem. Soc. 2007, 129, 8566-8576
31. Yamauchi, Y.; Suzuki, N.; Gupta, P.; Sato, K.; Fukata, N.; Murakami, M.; Shimizu, T.; Inoue, T.; Kimura, T. Sci. Technol. Adv. Mater. 2009, 10, 025005
32. Sharifi, M.; Kohler, C.; Tolle, P.; Frauenheim, T.; Wark, M. Small 2011, 7, 1086-1097
33. Lebed, P. J.; Savoie, J. D.; Florek, J.; Bilodeau, F.; Lariviere, D.; Kleitz, F. Chem. Mater. 2012, 24, 4166-4176
34. Mizoshita, N.; Yamanaka, K. I.; Hiroto, S.; Shinokubo, H.; Tani, T.; Inagaki, S. Langmuir 2012, 28, 3987-3994
35. Brunelli, N. A.; Venkatasubbaiah, K.; Jones, C. W. Chem. Mater. 2012, 24, 2433-2442
36. Liu, K.; Jin, R.; Cheng, T.; Xu, X.; Gao, F.; Liu, G.; Li, H. Chem.-Eur. J. 2012, 18, 15546-15553
37. Sasidharan, M.; Bhaumik, A. ACS Appl. Mater. Interfaces 2013, 5, 2618-2625
38. Nandi, M.; Mondal, J.; Sarkar, K.; Yamauchi, Y.; Bhaumik, A. Chem. Commun. 2011, 47, 6677-6679
39. Jain, S. L.; Modak, A.; Bhaumik, A. Green Chem. 2011, 13, 586-590
40. Suzuki, N.; Gupta, P.; Sukegawa, H.; Inomata, K.; Inoue, S.; Yamauchi, Y. J. Nanosci. Nanotechnol. 2010, 10, 6612-6617
41. Suzuki, N.; Yamauchi, Y. J. Nanosci. Nanotechnol. 2010, 10, 5759-5766
42. Yamauchi, Y.; Suzuki, N.; Sato, K.; Fukata, N.; Murakami, M.; Shimizu, T. Bull. Chem. Soc. Jpn. 2009, 82, 1039-1043
43. Alvim, H. G. O.; de Lima, T. B.; de Oliveira, H. C. B.; Gozzo, F. C.; de Macedo, J. L.; Abdenur, P. V.; Silva, W. A.; Neto, B. A. D. ACS Catal. 2013, 3, 1420-1430
44. Shiri, M. Chem. Rev. 2012, 112, 3508-3549
45. Yamauchi, Y.; Suzuki, N.; Radhakrishnan, L.; Wang, L. Chem. Rec. 2009, 9, 321-339
46. Yamauchi, Y. J. Ceram. Soc. Jpn. 2013, 121, 831-840
47. Lee, H. I.; Kim, J. M.; Stucky, G. D. J. Am. Chem. Soc. 2009, 131, 14249-14251
48. Kleitz, F.; Schmidt, W.; Schuth, F. Microporous Mesoporous Mater. 2003, 65, 1-29
49. Cychosz, K. A.; Guo, X.; Fan, W.; Cimino, R.; Gor, G. Y.; Tsapatsis, M.; Neimark, A. V.; Thommes, M. Langmuir 2012, 28, 12647-12654
50. Savithra, G. H. L.; Bowker, R. H.; Carrillo, B. A.; Bussell, M. E.; Brock, S. L. ACS Appl. Mater. Interfaces 2013, 5, 5403-5407
51. Kruk, M.; Jaroniec, M. Chem. Mater. 2001, 13, 3169-3183
52. Yamada, H.; Urata, C.; Aoyama, Y.; Osada, S.; Yamauchi, Y.; Kuroda, K. Chem. Mater. 2012, 24, 1462-1471
53. Modak, A.; Mondal, J.; Aswal, V. K.; Bhaumik, A. J. Mater. Chem. 2010, 20, 8099-8106
54. Chandra, D.; Yokoi, T.; Tatsumi, T.; Bhaumik, A. Chem. Mater. 2007, 19, 5347-5354
55. Pramanik, M.; Nandi, M.; Uyama, H.; Bhaumik, A. Catal. Sci. Technol. 2012, 2, 613-620
56. Vinu, A.; Ariga, K.; Mori, T.; Nakanishi, T.; Hishita, S.; Golberg, D.; Bando, Y. Adv. Mater. 2005, 17, 1648-1652
57. Lu, J.; Li, Y.; Deng, C. Nanoscale 2011, 3, 1225-1233
58. Borah, P.; Ma, X.; Nguyen, K. T.; Zhao, Y. Angew. Chem., Int. Ed. 2012, 51, 7756-7761
59. De, S.; Dutta, S.; Patra, A. K.; Rana, B. S.; Sinha, A. K.; Saha, B.; Bhaumik, A. Appl. Catal., A 2012, 435, 197-203
60. Roy, S. P.; Jadhavar, P. S.; Seth, K.; Sharma, K. K.; Chakraborti, A. K. Synthesis 2011, 14, 2261-2267
61. De Souza, R. O. M. A.; Penha, E. T. D.; Milagre, H. M. S.; Garden, S. J.; Esteves, P. M.; Eberlin, M. N.; Antunes, O. A. C. Chem.-Eur. J. 2009, 15, 9799-9804
62. Tayebeea, R.; Aminib, M. M.; Ghadamgahia, M.; Armaghan, M. J. Mol. Catal., A: Chem. 2013, 366, 266-274
63. Karimi, B.; Mirzaei, H. M.; Mobaraki, A. Catal. Sci. Technol. 2012, 2, 828-834