Different routes for preparing mesoporous organosilicas containing the trögers base and their textural and catalytic implications

Journal of Physical Chemistry C

Volumn 115, Issue 15, 2011, Pages 7573-7585

  Poli, Evelyne ^a   Merino, Estíbaliz ^a   Díaz, Urbano ^a   Brunel, Daniel ^a   Corma, Avelino ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ACTIVITY; ELEMENTAL ANALYSIS; HEXAGONAL STRUCTURES; KNOEVENAGEL REACTION; LONG-RANGE ORDERING; MAS-NMR SPECTROSCOPY; MESOPOROUS HYBRIDS; MESOPOROUS ORGANOSILICA MATERIALS; MESOPOROUS ORGANOSILICAS; NANO-STRUCTURED; NEUTRAL PH; NITROGEN SORPTION; ORGANOCATALYSTS; ORGANOSILICAS; PERIODIC MESOPOROUS ORGANOSILICAS; POSTSYNTHESIS GRAFTING; SBA-15 MATERIALS; SELF-ASSEMBLING PROCESS; SOL-GEL SYNTHESIS; STRUCTURAL FLEXIBILITIES; STRUCTURAL-DIRECTING AGENTS; STRUCTURATION; SYNTHESIS TEMPERATURES; THERMOGRAVIMETRY; VOLUMETRY;

CATALYST ACTIVITY; CHEMICAL ANALYSIS; FLEXIBLE STRUCTURES; HYBRID MATERIALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICA; SOL-GEL PROCESS; SORPTION; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

MESOPOROUS MATERIALS;

EID: 79954583955     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp2002854     Document Type: Article

References (111)

1. Knoevenagel, E. Ber. Deuts. Chem. Ges. 1896, 29, 172-174
2. ibid. 1898, 31, 730-737.
3. ibid. 1898, 31, 738-748.
4. ibid. 1898, 31, 2585-2595.
5. ibid. 1898, 31, 2596-2619.
6. Cope, A. C. J. Am. Chem. Soc. 1937, 59, 2327-2330
7. Charles, G. Bull. Soc. Chim. Fr. 1963, 8-9, 1576-1583
8. Jones, G. Organic Reactions; Wiley: New York, 1967; Vol. 15, pp 204 - 599.
9. Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 5861-5868
10. Jenner, G. Tetrahedron Lett. 2001, 42, 243-245
11. Fioravanti, S.; Pellacani, L.; Tardella, P. A.; Vergari, M. C. Org. Lett. 2008, 10, 1449-1451
12. Schuchardt, U.; Vargas, R. M.; Gelbard, G. J. Mol. Catal. A: Chem. 1995, 99, 65-70
13. Horváth, A. Tetrahedron Lett. 1996, 37, 4423-4426
14. Simoni, D.; Invidiata, F. P.; Manfredini, S.; Ferroni, R.; Lampronti, I.; Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1997, 38, 2749-2752
15. Gelbard, G.; Vielfaure-Joly, F. Tetrahedron Lett. 1999, 39, 2743-2746
16. Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic Eur. J. Org. Chem. 2000, 1077-1080
17. Bensa, D.; Brunel, J.-M.; Buono, G.; Rodriguez, J. Synlett. 2001, 5, 715-717
18. Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273-11283
19. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167-178
20. Basavaiah, D.; Rao, A. J. Tetrahedron Lett. 2003, 44, 4365-4368
21. Rafel, S.; Lealy, J. W. J. Org. Chem. 1997, 62, 1521-1522
22. Brzezinski, L. J.; Rafel, S.; Lealy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318
23. Garden, S. J.; Skakle, J. M. S. Tetrahedron Lett. 2002, 43, 3969-1972
24. Luque, R.; Macquarrie, D. J. Org. Biomol. Chem. 2009, 7, 1627-1632
25. Tröger, J. J. Prakt. Chem. 1887, 36, 225-245
26. Spielman, M. A. J. Am. Chem. Soc. 1935, 57, 583
27. Prelog, V.; Wieland., E. C. Helv. Chim. Acta 1944, 27, 1127-1134
28. Wilcox, C. S. Tetrahedron Lett. 1985, 26, 5749-5752
29. Pardo, C.; Ramos, M.; Fruchier, A.; Elguero, J. Magn. Reson. Chem. 1996, 34, 708-710
30. Cowart, M. D.; Sucholeiki, I.; Bukownik, R. R.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 6204-6210
31. Bag, G. B. Curr. Sci. 1995, 68, 279-288
32. Allen, P. R.; Reek, J. N. H.; Try, A. C.; Crossley, M. J. Tetrahedron: Asymmetry 1997, 8, 1161-1164
33. Tatiboueøt, A.; Demeunynck, M.; Andraud, C.; Collet, A.; Lhomme, J. Chem. Commun 1999, 161-162
34. Demeunynck, M.; Tatiboueøt, A. In Recent developments in Trogers base chemistry. Progress in Heterocyclic Chemistry; Gribble, G. W.; Gilchrist, J. L., Eds.; Pergamon: Oxford, U.K., 1999; Vol. 11, pp 1 - 20.
35. Valík, M.; Strongin, R. M.; Král, V. Supramolecular Chem. 2005, 17, 347-367
36. Dolenský, B.; Elguero, J.; Král, V.; Pardo, C.; Valík, M. Adv. Heterocycl. Chem. 2007, 93, 1-56
37. Didier, D.; Sergeyev, S. Targets Heterocycl. Syst. 2007, 11, 258-283
38. Sergeyev, S. Helv. Chim. Acta 2009, 92, 415-444
39. Sergeyev, S.; Didier, D.; Boitsov, V.; Teshome, A.; Asselberghs, I.; Clays, K.; Velde, C. M. L. V.; Plaquet, A.; Champagne, B. Chem.-Eur. J. 2010, 16, 8181-8190
40. Minder, B; Schürch, M.; Mallat, T.; Baiker, A. Catal. Lett. 1995, 31, 143-151
41. Schutz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035
42. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229
43. Goldberg, Y.; Alper, H. Tetrahdron Lett. 1995, 36, 369-372
44. Harmata, M.; Kahraman, M. Tetrahedron: Asymmetry 2000, 11, 2875-2879
45. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823
46. Kitamura, M.; Suga, S.; Kawai, K.; Noyori J. Am. Chem. Soc. 1986, 108, 6071-6072
47. Soai, K; Niwa, S. Chem. Rev. 1992, 92, 833-856
48. Shen, Y.-M.; Zhao, M.-X.; Xu, J.; Shi, Y. Angew. Chem., Int. Ed. 2000, 45, 8005-8008
49. Wu, H.; Chen, X.-m.; Wan, Y.; Ye, L.; Xin, H.-q. X.; Xu, H.-h.; Yue, C.-h.; Pang, L.-l.; Ma, R.; Shi, D.-q. Tetrahedron Lett. 2009, 50, 1062-1065
50. Didier, D.; Sergeyev, S. ARKIVOC 2009, xiv, 124-134
51. Wepster, B. M. Rec. Trav. Chim. Pays-Bas 1953, 72, 661-672
52. Du, X.; Sun, Y.; Tan, B.; Teng, Q.; Yao, X.; Su, C.; Wang, W. Chem. Commun. 2010, 46, 970-972
53. Banet, P.; Marcotte, N.; Lerner, D. A.; Brunel, D. Langmuir 2008, 24, 9030-9037
54. Fajula, F.; Brunel, D. Microporous Mesoporous Mater. 2001, 48, 119-125
55. del Pozo, C.; Corma, A.; Iglesias, M.; Sánchez, F. Organometallics 2010, 29, 4491-4498
56. Shea, K. J.; Kenneth, J.; Loy, D. A.; Webster, O. W. Chem. Mater. 1989, 1, 572-574
57. Shea, K. J.; Loy, D. A.; Webster, O. W. J. Am. Chem. Soc. 1992, 114, 6700-6710
58. Corriu, R. J. P.; Moreau, J. J. E.; Thépot, Ph.; Wong Chi Man, M. Chem. Mater. 1992, 4, 1217-24
59. Corriu, R. J. P.; Hesemann, P.; Lanneau, G. F. Chem. Commun. 1996, 1845-1846
60. Inagaki, S.; Guan, S.; Fukushima, Y.; Ohsuna, T.; Terasaki, O. J. Am. Chem. Soc. 1999, 121, 9611-9614
61. Asefa, T.; MacLachlan, M. J.; Coombs, N; Ozin, G. A. Nature 1999, 402, 867-871
62. Melde, B. J.; Holland, B. T.; Blandford, C. F.; Stein, A. Chem. Mater. 1999, 11, 3302-3308
63. Yang, Q.; Kapoor, M. P.; Inagaki, S. J. Am. Chem. Soc. 2002, 124, 9694-9695
64. Zhu, H.; Jones, D. J.; Zajac, J.; Dutartre, R.; Rhomari, M.; Rozière, J. Chem. Mater. 2002, 14, 4886-4894
65. Fujita, S.; Inagaki, S. Chem. Mater. 2008, 20, 891-90
66. Ozin, G. O.; Hunks, W. J. J. Mater. Chem. 2005, 15, 3716-3724
67. Baleizao, C.; Gigante, B.; Das, D.; Alvaro, M.; Garcia, H.; Corma, A. Chem. Commun. 2003, 1860-1861
68. Maegawa, Y.; Goto, Y.; Inagaki, S.; Shimada, T. Tetrahedron Lett. 2006, 47, 6957-6960
69. Morell, J.; Chatterjee, S.; Klar, P. J.; Mauder, D.; Shenderovitch, I.; Hoffmann, F.; Fröba, M. Chem.-Eur. J. 2008, 14, 5935-5940
70. Kuschel, A.; Sievers, H.; Polarz, S. Angew. Chem., Int. Ed. 2008, 47, 9513-9517
71. Kuschel, A.; Polarz, S. Adv. Funct. Mater. 2008, 18, 1272-1280
72. MacQuarrie, S.; Thompson, M. P.; Blanc, A.; Mosey, N. J.; Lemieux, R. P.; Crudden, C. M. J. Am. Chem. Soc. 2008, 130, 14099-14101
73. Takeda, H.; Goto, Y.; Maegawa, Y.; Ohsuna, T.; Tani, T.; Matsumoto, T.; Inagaki, S. Chem. Commun. 2009, 6032-6034
74. Yang, Q.; Liu, J.; Zhang, L.; Li, C. J. Mater. Chem. 2009, 19, 1945-1945
75. Nguyen, T. P.; Hesemann, P.; Gaveau, Ph.; Moreau, J. J. E. J. Mater. Chem. 2009, 19, 4164-4171
76. Cho, E.-B.; Kim, D.; Jaroniec, M. Langmuir 2009, 25, 13258-13263
77. El Kadib, A.; Hesemann, P.; Molvinger, K.; Brandner, J.; Biolley, C.; Moreau, J. J. E.; Brunel, D. J. Am. Chem. Soc. 2009, 131, 2882-2892
78. Cho, E.-B.; Han, O. H.; Kim, S.; Kim, D.; Jaroniec, M. Chem. Commun. 2010, 46, 4568-4570
79. Corriu, R. J. P.; Mehdi, A.; Reyé, C. Chem. Soc. Rev. 2005, 15, 4285-4294
80. Brinker, C. J.; Schere, G. W. Sol-Gel Science; Academic; Boston, 1990.
81. Corriu, R. J. P.; Mehdi, A.; Reyé, C.; Thieuleux, C. Chem. Mater. 2004, 16, 159-166
82. Reale, E.; Leyva, A.; Corma, A.; Martínez, C; García, H.; Rey, F. J. Mater. Chem. 2005, 15, 1742-1754
83. Díaz, U.; García, T.; Velty, A.; Corma, A. J. Mater. Chem. 2009, 19, 5970-5979
84. Mokaya, R.; Jones, W. J. Mater. Chem. 1998, 8, 2819-2826
85. Zhao, D.; Huo, Q.; Feng, J.; Chmelka, B. F.; Stucky, G. D. J. Am. Chem. Soc. 1998, 120, 6024-6036
86. Brunauer, S.; Emmet, P. H.; Teller, E. J. Am. Chem. Soc. 1938, 60, 309-319
87. Broekhoff, J. C. P.; De Boer, J. H. J. Catal. 1968, 10, 377-390
88. Jaroniec, M.; Solovyov, L. A. Langmuir 2006, 22, 6757-6760
89. Jensen, J.; Wärnmark, K. Synthesis 2001, 1873-1877
90. Maegawa, Y.; Goto, Y.; Inagaki, S.; Shimada, T. Tetrahedron Lett. 2006, 47, 6957-6960
91. Abramson, S.; Laspéras, M.; Galarneau, A.; Desplantier-Giscard, D.; Brunel, D. Chem. Commun. 2000, 1773-1774
92. Martin, T.; Galarneau, A.; Brunel, D.; Izard, V.; Hulea, V.; Blanc, A. C.; Abramson, S.; Di Renzo, F.; Fajula, F. Sud. Surf. Sci. Catal. 2001, 135, 4621-4628
93. Didier, D.; Tylleman, B.; Lambert, N.; Velde, M. L. V.; Blockhus, F.; Collas, A.; Sergeyev, S. Tetrahedron 2008, 64, 6252-6262
94. Jensen, J.; Tejler, J.; Wärnmark, K. J. Org. Chem. 2002, 67, 1873-1877
95. Faroughi, M.; Try, A. C.; Turner, P. Acta Crystallogr. 2006, E62, o3674-o3675
96. Faroughi, M.; Jensen, P.; Try, A. C. ARKIVOC 2009, (ii), 269-280
97. Faroughi, M.; Zhu, K.-X.; Jensen, P.; Craig, D. C.; Try, A. C. Eur. J. Org. Chem. 2009, 4266-4272
98. Murata, M.; Ishikura, M.; Nagata, M.; Watanabe, S.; Masuda, Y. Org. Lett. 2002, 4, 1843-1845
99. Sergeyev, S.; Schär, M.; Seiler, P.; Lukoyanova, O.; Echegoyen, L.; Diederich, F. Chem.-Eur. J. 2005, 11, 2284-2294
100. Bew, S. P.; Legentil, L.; Scholier, V.; Sharma, S. V. Chem. Commun 2007, 389-391
101. Jensen, J.; Strozyk, M.; Wärnmark, K. J. Heterocyclic Chem. 2003, 40, 373-375
102. Didier, D.; Sergeyev, S. Eur. J. Org. Chem. 2007, 3905-3910
103. Cudero, J.; Jiménez, P.; Marcos, C.; Pardo, C.; Ramos, M.; Elguero, J.; Fruchier, A. Magn. Reson. Chem. 1996, 34, 318-323
104. Elguero, J.; Fruchier, A.; Mas, T.; Pardo, C. Magn. Reson. Chem. 2005, 43, 665-669
105. Wiench, J. W.; Avadhut, Y. S.; Maity, N.; Bhaduri, S.; Kumar Lahiri, G.; Pruski, M.; Ganapathy, S. J. Phys. Chem. B 2007, 111, 3877-3885
106. Massiot, D.; Fayon, F.; Capron, M.; King, I.; Le Calvé, S.; Alonso, B.; Durand, J.-O.; Bujoli, B.; Gan, Z.; Hoatson, G. Magn. Reson. Chem. 2002, 40, 70-76
107. Yoshina-Ishii, C.; Asefa, T.; Coombs, N.; MacLachlan, M. J.; Ozin, G. A. Chem. Commun. 1999, 2539-2540
108. Brunel, D. Microporous Mesoporous Mater. 1999, 27, 329-344
109. Macquarrie, D. J.; Clark, J. H.; Tailland, K. A.; Utting, K. A. J. Mater. Chem. 2001, 11, 1843-1849
110. Sharma, K. K.; Buckley, R. P.; Asefa, T. Langmuir 2008, 24, 14306-14320
111. Hruby, S. L.; Shanks, B. H. J. Catal. 2009, 263, 181-188