Copper-catalyzed oxybromination and oxychlorination of primary aromatic amines using LiBr or LiCl and molecular oxygen

Advanced Synthesis and Catalysis

Volumn 350, Issue 13, 2008, Pages 2052-2058

  Menini, Luciano ^a   Da Cruz Santos, Joyce C ^a   Gusevskaya, Elena V ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Amines; Copper; Oxybromination; Oxychlorination; Oxygen

Indexed keywords

EID: 53849123663     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800223     Document Type: Article

References (35)

1. Electrophilic Aromatic Substitution, (Ed.: R. Taylor), Wiley, Chichester, 1990.
2. D. He, H. Shi, Y. Wu, B.-Q. Xu, Green Chem. 2007, 9, 849.
3. G. Rothenberg, J. H. Clark, Org. Process Res. Dev. 2000, 4, 270.
4. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
5. E. Baumgarten, A. Fiebes, A. Stumpe, React. Funct. Polym. 1997, 33, 71.
6. Y. Sato, H. Sato, S. Ototake, S. Ynada, (Nippon Kayaku Company), Japanese Patent 63077844, 1988.
7. M. B. Smith, J. March, Advanced Organic Chemistry. Reactions, Mechanisms and Structure, 5th edn., Willey, New York, 2001, p 705.
8. B. Das, K. Vetkateswarlu, M. Kroshnaiah, H. Holla, Tetrahedron Lett. 2006, 47, 8693.
9. B. Das, K. Vetkateswarlu, A. Majhi, V. Siddaiah, K. R. Reddy, J. Mol. Catal. 2007, 267, 30.
10. M. M. Heravi, N. Abdolhosseini, H. A. Oskooie, Tetrahedron Lett. 2006, 46, 8959.
11. M. J. Guo, L. Varady, D. Fokas, C. Baldino, L. Yu, Tetrahedron Lett. 2006, 47, 3889.
12. B. M. Choudary, Y. Sudha, P. N. Reddy, Synlett 1994, 450.
13. G. Rothenberg, J. H. Clark, Green Chem. 2000, 2, 248.
14. D. Roche, K. Prasad, O. Repic, T. J. Blacklock, Tetrahedron Lett. 2000, 41, 2083.
15. U. Bora, G. Bose, M. K. Chaudhuri, S. S. Dhar, R. Gopinath, A. T. Khan, B. K. Patel, Organic Lett. 2000, 2, 247.
16. N. Narender, P. Srinivasu, S. J. Kulkarni, K. V. Raghavan, Stud. Surf. Sci. Catal. 2001, 135, 3745.
17. K. V. V. Krishna Mohan, N. Narender, P. Srinivasu, S. J. Kulkarni, K. V. Raghavan, Synth. Commun. 2004, 34, 2143.
18. S. Singhal, S. L. Jain, B. Sain, J. Mol. Catal. A 2006, 258, 198.
19. B. Ganchegui, W. Leitner, Green Chem. 2007, 9, 26.
20. R. Neumann, I. Assael, J. Chem. Soc. Chem. Commun. 1988, 1285.
21. J. Xiong, J.-X. Chen, J.-Y. Zhang, Huaxue Shiji 2006, 28, 331.
22. R. Raja, P. Ratnasamy, J. Catal. 1997, 170, 244.
23. R. C. Mills, T. L. Chuck, (General Electric Company), U. S. Patent 6,693,221, 2004.
24. G. L. Soloveichik, (General Electric Company), U. S. Patent 2005,049,441, 2005.
25. G. Zhang, R. Liu, Q. Xu, L. Ma, X. Liang, Adv. Synth. Catal. 2006, 348, 862.
26. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790.
27. L. Menini, E. V. Gusevskaya, Chem. Commun. 2006, 209.
28. L. Menini, E. V. Gusevskaya, Appl. Catal. A 2006, 309, 122.
29. L. Menini, L. A. Parreira, E. V. Gusevskaya, Tetrahedron Lett. 2007, 38, 6401.
30. K. Kinoshita, Bull. Chem. Soc. Jpn. 1959, 32, 780.
31. E. G. Derouane, J. N. Braham, R. Hubin, J. Catal. 1974, 35, 196.
32. R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981, p 391.
33. J. I. van der Vlugt, F. Meyer, Top. Organomet. Chem. 2007, 22, 191.
34. N. Toshima, H. Yan, M. Ishiwatari, Bull. Chem. Soc. Jpn. 1994, 67, 1947.
35. J. McMurry, Organic Chemistry, 2nd edn., Brooks/Cole, Pasific Grove, CA, 1988, p 939.