Titania-supported iridium subnanoclusters as an efficient heterogeneous catalyst for direct synthesis of quinolines from nitroarenes and aliphatic alcohols

Angewandte Chemie - International Edition

Volumn 50, Issue 43, 2011, Pages 10216-10220

  He, Lin ^a   Wang, Jian Qiang ^b   Gong, Ya ^a   Liu, Yong Mei ^a   Cao, Yong ^a   He, He Yong ^a   Fan, Kang Nian ^a  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF APPLIED PHYSICS   (China)

Author keywords

alcohols; arenes; cluster compounds; heterogeneous catalysis; iridium

Indexed keywords

ALIPHATIC ALCOHOL; ARENES; CLUSTER COMPOUNDS; DIRECT SYNTHESIS; HETEROGENEOUS CATALYST; IRIDIUM CLUSTERS; NITROARENES; QUINOLINE DERIVATIVE; REACTIVE FUNCTIONAL GROUPS; TITANIA;

CATALYSIS; CATALYSTS; FUNCTIONAL GROUPS; TITANIUM DIOXIDE;

IRIDIUM;

EID: 80054038813     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104089     Document Type: Article

References (59)

1. G. Schmid, Nanoparticles: From Theory to Application, Wiley-VCH, Weinheim, 2004
2. D. Astruc, Nanoparticles and Catalysis, Wiley-VCH, Weinheim, 2008
3. D. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. 2005, 117, 8062-8083
4. Angew. Chem. Int. Ed. 2005, 44, 7852-7872
5. C. Burda, X. Chen, R. Narayanan, M. A. El-Sayed, Chem. Rev. 2005, 105, 1025-1102.
6. H. Tsunoyama, H. Sakurai, Y. Negishi, T. Tsukuda, J. Am. Chem. Soc. 2005, 127, 9374-9375
7. S. Panigrahi, S. Basu, S. Praharaj, S. Pande, S. Jana, A. Pal, S. K. Ghosh, T. Pal, J. Phys. Chem. C 2007, 111, 4596-4605
8. C. M. Y. Yeung, K. M. K. Yu, Q. J. Fu, D. Thompsett, M. I. Petch, S. C. Tsang, J. Am. Chem. Soc. 2005, 127, 18010-18011
9. Y. M. Liu, H. Tsunoyama, T. Akita, S. H. Xie, T. Tsukuda, ACS Catal. 2011, 1, 2-6.
10. M. Moreno-Manas, R. Pleixats, Acc. Chem. Res. 2003, 36, 638-643
11. A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 2002, 102, 3757-3778
12. K. Kaneda, K. Ebitani, T. Mizugaki, K. Mori, Bull. Chem. Soc. Jpn. 2006, 79, 981-1016
13. T. Oishi, K. Yamaguchi, N. Mizuno, Angew. Chem. 2009, 121, 6404-6406
14. Angew. Chem. Int. Ed. 2009, 48, 6286-6288
15. L. He, L. C. Wang, H. Sun, J. Ni, Y. Cao, H. Y. He, K. N. Fan, Angew. Chem. 2009, 121, 9702-9705
16. Angew. Chem. Int. Ed. 2009, 48, 9538-9541.
17. K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2004, 126, 5662-5663
18. M. J. Climent, A. Corma, S. Iborra, L. L. Santos, Chem. Eur. J. 2009, 15, 8834-8841
19. H. Sun, F. Z. Su, J. Ni, Y. Cao, H. Y. He, K. N. Fan, Angew. Chem. 2009, 121, 4454-4457
20. Angew. Chem. Int. Ed. 2009, 48, 4390-4393.
21. F. X. Felpin, E. Fouquet, ChemSusChem 2008, 1, 718-724
22. M. J. Climent, A. Corma, S. Iborra, ChemSusChem 2009, 2, 500-506.
23. M. Zhang, H.-F. Jiang, H. Neumann, M. Beller, P. H. Dixneuf, Angew. Chem. 2009, 121, 1709-1712
24. Angew. Chem. Int. Ed. 2009, 48, 1681-1684
25. C. M. Wei, C. J. Li, J. Am. Chem. Soc. 2003, 125, 9584-9585
26. F. Rodriguez, F. J. Fananas, Chem. Asian J. 2009, 4, 1036-1048.
27. G. Jones, Comprehensive Heterocyclic Chemistry, Pergamon, New York, 1984
28. C. Theeraladanon, M. Arisawa, M. Nakagawa, A. Nishida, Tetrahedron: Asymmetry 2005, 16, 827-831
29. Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu, C. C. Tzeng, J. Med. Chem. 2001, 44, 2374-2377
30. G. Roma, M. D. Braccio, G. Grossi, F. Mattioli, M. Ghia, Eur. J. Med. Chem. 2000, 35, 1021-1035.
31. B. Jiang, Y. G. Si, J. Org. Chem. 2002, 67, 9449-9451
32. A. K. Agrawal, S. A. Jenekhe, Macromolecules 1991, 24, 6806-6808
33. X. Zhang, A. S. Shetty, S. A. Jenekhe, Macromolecules 1999, 32, 7422-7429.
34. R. H. F. Manske, M. Kukla, Org. React. 1953, 7, 59-98.
35. S. E. Denmark, S. Venkatraman, J. Org. Chem. 2006, 71, 1668-1676.
36. E. A. Steck, L. L. Hallock, A. J. Holland, L. T. Fletcher, J. Am. Chem. Soc. 1948, 70, 1012-1015.
37. J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M. C. Carreiras, E. Soriano, Chem. Rev. 2009, 109, 2652-2671.
38. H. R. Henze, D. W. Carroll, J. Am. Chem. Soc. 1954, 76, 4580-4584.
39. V. V. Kouznetsov, L. Y. Vargas Méndez, C. M. Meléndez Gõmez, Curr. Org. Chem. 2005, 9, 141-161.
40. R. S. Downing, P. J. Kunkeler, H. van Bekkum, Catal. Today 1997, 37, 121-136.
41. L. Li, W. D. Jones, J. Am. Chem. Soc. 2007, 129, 10707-10713
42. S. E. Diamond, A. Szalkiewicz, F. Mares, J. Am. Chem. Soc. 1979, 101, 490-491
43. C. S. Cho, B. H. Oh, S. C. Shim, Tetrahedron Lett. 1999, 40, 1499-1500
44. C. S. Yi, S. Y. Yun, J. Am. Chem. Soc. 2005, 127, 17000-17006
45. K. Motokura, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett. 2004, 45, 6029-6032.
46. Y. Watanabe, Y. Tsuji, J. Shida, Bull. Chem. Soc. Jpn. 1984, 57, 435-438
47. W. J. Boyle, F. Mare, Organometallics 1982, 1, 1003-1006
48. K. Selvam, M. Swaminathan, Catal. Commun. 2011, 12, 389-393.
49. L. A. Oro, C. Claver, Iridium Complexes in Organic Synthesis Wiley-VCH, Weinheim, 2009
50. X. F. Wu, J. K. Liu, X. H. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. W. Ruan, J. L. Xiao, Angew. Chem. 2006, 118, 6870-6874
51. Angew. Chem. Int. Ed. 2006, 45, 6718-6722
52. A. Zhao, B. C. Gates, J. Am. Chem. Soc. 1996, 118, 2458-2469
53. M. De bruyn, S. Coman, R. Bota, V. I. Parvulescu, D. E. De Vos, P. A. Jacobs, Angew. Chem. 2003, 115, 5491-5494
54. Angew. Chem. Int. Ed. 2003, 42, 5333-5336.
55. H. Tsunoyama, H. Sakurai, T. Tsukuda, Chem. Phys. Lett. 2006, 429, 528-532
56. A. M. Argo, J. F. Odzak, B. C. Gates, J. Am. Chem. Soc. 2003, 125, 7107-7115.
57. M. A. Fakhfakh, A. Fournet, E. Prina, J. F. Mouscadet, X. Franck, R. Hocquemiller, B. Figadere, Bioorg. Med. Chem. 2003, 11, 5013-5023.
58. A. Walker, W. E. Baldwin, H. I. Thayer, B. B. Corson, J. Org. Chem. 1951, 16, 1805-1808.
59. C. Perez-Melero, A. B. S. Maya, B. D. Rey, R. Pelaez, E. Caballero, M. Medarde, Bioorg. Med. Chem. 2004, 14, 3771-3774.