Arenesulfonic acid-functionalized mesoporous silica decorated with titania: A heterogeneous catalyst for the one-pot photocatalytic synthesis of quinolines from nitroaromatic compounds and alcohols

ACS Catalysis

Volumn 3, Issue 4, 2013, Pages 565-572

  Hakki, Amer ^a   Dillert, Ralf ^a   Bahnemann, Detlef W ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

mesoporous materials; photocatalysts; quinoline; reaction mechanism

Indexed keywords

ARENESULFONIC ACID-FUNCTIONALIZED MESOPOROUS SILICAS; BI-FUNCTIONAL CATALYSTS; NITROAROMATIC COMPOUND; PHOTOCATALYTIC SYNTHESIS; PHOTOGENERATED ELECTRONS; QUINOLINE; REACTION MECHANISM; TETRA-ETHYL-ORTHO-SILICATE;

CATALYSTS; CONDENSATION; CYCLIZATION; MESOPOROUS MATERIALS; NITROGEN COMPOUNDS; PHOTOCATALYSTS; SYNTHESIS (CHEMICAL); TITRATION;

TITANIUM DIOXIDE;

EID: 84875915101     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs300736x     Document Type: Article

References (53)

1. Ohno, T.; Tsubota, T.; Kakiuchi, K.; Miyayarna, S.; Sayama, K. J. Mol. Catal. A: Chem. 2006, 245, 47-54
2. Lang, X. J.; Ji, H. W.; Chen, C. C.; Ma, W. H.; Zhao, J. C. Angew. Chem., Int. Ed. 2011, 50, 3934-3937
3. Pehlivanugullari, H. C.; Sumer, E.; Kisch, H. Res. Chem. Intermed. 2007, 33, 297-309
4. Park, K. H.; Joo, H. S.; Ahn, K. I.; Jun, K. Tetrahedron Lett. 1995, 36, 5943-5946
5. Cermenati, L.; Richter, C.; Albini, A. Chem. Commun. 1998, 805-806
6. Hakki, A.; Dillert, R.; Bahnemann, D. Catal. Today 2009, 144, 154-159
7. Ohtani, B.; Osaki, H.; Nishimoto, S.; Kagiya, T. J. Am. Chem. Soc. 1986, 108, 308-310
8. Ohno, T.; Tokieda, K.; Higashida, S.; Matsumura, M. Appl. Catal., A 2003, 244, 383-391
9. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129-2137
10. Zhang, X. J.; Shetty, A. S.; Jenekhe, S. A. Macromolecules 1999, 32, 7422-7429
11. Ahmed, E.; Earmme, T.; Jenekhe, S. A. Adv. Funct. Mater. 2011, 21, 3889-3899
12. Earmme, T.; Ahmed, E.; Jenekhe, S. A. Adv. Mater. 2010, 22, 4744-4748
13. Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 59-98
14. Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668-1676
15. Brouet, J. C.; Gu, S.; Peet, N. P.; Williams, J. D. Synth. Commun. 2009, 39, 1563-1569
16. Marco-Contelles, J.; Perez-Mayoral, E.; Samadi, A.; Carreiras, M. D.; Soriano, E. Chem. Rev. 2009, 109, 2652-2671
17. Buuhoi, N. P.; Royer, R.; Xuong, N. D.; Jacquignon, P. J. Org. Chem. 1953, 18, 1209-1224
18. Monrad, R. N.; Madsen, R. Org. Biomol. Chem. 2011, 9, 610-615
19. Cho, C. S.; Kim, T. K.; Kim, B. T.; Kim, T. J.; Shim, S. C. J. Organomet. Chem. 2002, 650, 65-68
20. Li, L.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 10707-10713
21. Akbari, J.; Heydari, A.; Kalhor, H. R.; Kohan, S. A. J. Comb. Chem. 2010, 12, 137-140
22. Cho, C. S.; Kim, T. G.; Yoon, N. S. Appl. Organomet. Chem. 2010, 24, 291-293
23. He, L.; Wang, J. Q.; Gong, Y.; Liu, Y. M.; Cao, Y.; He, H. Y.; Fan, K. N. Angew. Chem., Int. Ed. 2011, 50, 10216-10220
24. Selvam, K.; Swaminathan, M. Tetrahedron Lett. 2010, 51, 4911-4914
25. Lopez, T.; Bosch, P.; Tzompantzi, F.; Gomez, R.; Navarrete, J.; Lopez-Salinas, E.; Llanos, M. E. Appl. Catal., A 2000, 197, 107-117
26. Li, Z. L.; Wnetrzak, R.; Kwapinski, W.; Leahy, J. J. ACS Appl. Mater. Interfaces 2012, 4, 4499-4505
27. Zhao, H. Y.; Bennici, S.; Shen, J. Y.; Auroux, A. J. Catal. 2010, 272, 176-189
28. Ikeda, S.; Kobayashi, H.; Ikoma, Y.; Harada, T.; Torimoto, T.; Ohtani, B.; Matsumura, M. Phys. Chem. Chem. Phys. 2007, 9, 6319-6326
29. Oki, A. R.; Xu, Q.; Shpeizer, B.; Clearfield, A.; Qiu, X.; Kirumakki, S.; Tichy, S. Catal. Commun. 2007, 8, 950-956
30. Kim, Y. K.; Kim, E. Y.; Whang, C. M.; Kim, Y. H.; Lee, W. I. J. Sol-Gel Sci. Technol. 2005, 33, 87-91
31. Pan, J. H.; Zhao, X. S.; Lee, W. I. Chem.-Eng. J. 2011, 170, 363-380
32. Zhao, D. Y.; Feng, J. L.; Huo, Q. S.; Melosh, N.; Fredrickson, G. H.; Chmelka, B. F.; Stucky, G. D. Science 1998, 279, 548-552
33. Clark, J. H. Acc. Chem. Res. 2002, 35, 791-797
34. Mbaraka, I. K.; Shanks, B. H. J. Catal. 2006, 244, 78-85
35. Liu, J.; Yang, Q. H.; Kapoor, M. P.; Setoyama, N.; Inagaki, S.; Yang, J.; Zhang, L. J. Phys. Chem. B 2005, 109, 12250-12256
36. Jackson, M. A.; Mbaraka, I. K.; Shanks, B. H. Appl. Catal., A 2006, 310, 48-53
37. Rac, B.; Molnar, A.; Forgo, P.; Mohai, M.; Bertoti, I. J. Mol. Catal. A: Chem. 2006, 244, 46-57
38. Dufaud, V.; Davis, M. E. J. Am. Chem. Soc. 2003, 125, 9403-9413
39. Das, D.; Lee, J. F.; Cheng, S. F. Chem. Commun. 2001, 2178-2179
40. Van Rhijn, W. M.; De Vos, D. E.; Sels, B. F.; Bossaert, W. D.; Jacobs, P. A. Chem. Commun. 1998, 317-318
41. Melero, J. A.; Stucky, G. D.; van Grieken, R.; Morales, G. J. Mater. Chem. 2002, 12, 1664-1670
42. Mehrvar, M.; Anderson, W. A.; Moo-Young, M. Int. J. Photoenergy 2002, 4, 141-146
43. Wang, X. G.; Cheng, S. F.; Chan, J. C. C.; Chao, J. C. H. Microporous Mesoporous Mater. 2006, 96, 321-330
44. Xu, Z. P.; Braterman, P. S. J. Mater. Chem. 2003, 13, 268-273
45. Pejov, L.; Ristova, M.; Soptrajanov, B. Spectrochim. Acta, Part A 2011, 79, 27-34
46. Yang, Q. H.; Kapoor, M. P.; Shirokura, N.; Ohashi, M.; Inagaki, S.; Kondo, J. N.; Domen, K. J. Mater. Chem. 2005, 15, 666-673
47. Bibent, N.; Mehdi, A.; Silly, G.; Henn, F.; Devautour-Vinot, S. Eur. J. Inorg. Chem. 2011, 3214-3225
48. Zhao, W.; Salame, P.; Launay, F.; Gedeon, A.; Hao, Z. J. Porous Mater 2008, 15, 139-143
49. Ohtani, B.; Osaki, H.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1985, 1075-1078
50. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656-670
51. Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1964, 2221
52. Leir, C. M. J. Org. Chem. 1977, 42, 911-913
53. Bello, D.; Ramon, R.; Lavilla, R. Curr. Org. Chem. 2010, 14, 332-356