1,2,3,4-Tetrahydro-8-hydroxyquinoline-promoted copper-catalyzed coupling of nitrogen nucleophiles and aryl bromides

Journal of Organic Chemistry

Volumn 73, Issue 21, 2008, Pages 8639-8642

  Wang, Huifeng ^a   Li, Yaming ^a   Sun, Fangfang ^a   Feng, Yang ^a   Jin, Kun ^a   Wang, Xiuna ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; COPPER; LIGANDS; NUCLEOPHILES;

ACCELERATING EFFECTS; AMINO-PHENOLS; ARYL BROMIDES; CATALYZED COUPLINGS; CHEMICAL EQUATIONS; HYDROXYQUINOLINE; MILD CONDITIONS; NITROGEN NUCLEOPHILES;

BROMINE COMPOUNDS;

1,2,3,4 TETRAHYDRO 8 HYDROXYQUINOLINE; 2 AMINOPHENOL; 8 QUINOLINOL DERIVATIVE; BROMINE DERIVATIVE; COPPER; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CROSS COUPLING REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION;

AMINOPHENOLS; BENZENE DERIVATIVES; CATALYSIS; COPPER; CROSS-LINKING REAGENTS; HYDROCARBONS, BROMINATED; HYDROXYQUINOLINES; NITROGEN;

EID: 55249105440     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015488     Document Type: Article

References (37)

1. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599.
2. (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
3. (b) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
4. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
5. (d) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096.
6. (a) Klapars, A.; Huang, X. H.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
7. (b) Buchwald, S. L.; Klapars, A.; Antilla, J. C.; Job, G. E.; Wolter, M.; KwongF. Y.; Nordmann, G.; Hennessy, E. J. WO 02/085838, 2002.
8. (a) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
9. (b) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. - Eur. J. 2004, 10, 5607.
10. (c) Taillefer, M.; Cristau, H. J.; Cellier, P. P.; Spindler, J. F. WO 03/53225, 2003.
11. (d) Taillefer, M.; Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Ouali, A. WO 03/101966, 2003.
12. (a) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
13. (b) Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190.
14. (a) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
15. (b) Sreedhar, B.; Kumar, K. B. S.; Srinivas, P.; Balasubrahmanyam, V.; Venkanna, G. T. J. Mol. Catal. A: Chem. 2007, 265, 183.
16. (c) Mao, J.; Guo, J.; Song, H.; Ji, S. Tetrahedron 2008, 64, 1383.
17. Ma, H. C.; Jiang, X. Z. J. Org. Chem. 2007, 72, 8943.
18. (a) Xu, L.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2005, 61, 6553.
19. (b) Rao, H. H.; Jin, Y.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Chem. - Eur. J. 2006, 12, 3636.
20. (a) Wu, Y. P.; Wang, C. J.; Wang, Y. Y.; Liu, P.; Wu, W. P.; Shi, Q. Z.; Peng, S. M. Polyhedron 2006, 25, 3533.
21. (b) Zhu, L. B.; Cheng, L.; Zhang, Y. X.; Xie, R. G.; You, J. S. J. Org. Chem. 2007, 72, 2737.
22. (a) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
23. (b) Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
24. (c) Nandurkar, N. S.; Bhanushali, M. J.; Bhor, M. D.; Bhanage, B. M. Tetrahedron Lett. 2007, 48, 6573.
25. (d) Jiang, D. S.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. J. Org. Chem. 2007, 72, 672.
26. (a) Kantam, M. L.; Venkanna, G. T.; Sridhar, C.; Kumar, K. B. S. Tetrahedron Lett. 2006, 47, 3897.
27. (b) Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948.
28. (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
29. (b) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
30. (c) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
31. Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703.
32. Lu, Z. K.; Twieg, R. J.; Huang, S. P. D. Tetrahedron Lett. 2003, 44, 6289.
33. (a) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 43, 7143.
34. (b) Liu, Y.; Chen, C.; Yang, L. Tetrahedron Lett. 2006, 47, 9275.
35. Liu, L. B.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. Org. Chem. 2005, 70, 10135.
36. (b) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
37. (c) Pu, Y.; Ku, Y.; Grieme, T.; Henry, R.; Bhatia, A. Tetrahedron Lett. 2006, 47, 149.