Cu-Al hydrotalcite: An efficient and reusable ligand-free catalyst for the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines

Synthesis

Volumn , Issue 15, 2009, Pages 2517-2522

  Sreedhar, B ^a   Arundhathi, R ^a   Linga Reddy, P ^a   Amarnath Reddy, M ^a   Lakshmi Kantam, M ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aryl chloride; Copper; Coupling; Hydrotalcite; N alkylated arylated amines; Reusable catalyst

Indexed keywords

AL HYDROTALCITE; ALMOST CONSISTENT; ARYL CHLORIDE; HETEROCYCLIC AMINES; HYDROTALCITE; HYDROTALCITE CATALYSTS; LIGAND-FREE; N-ALKYLATED/ARYLATED AMINES; NUMBER OF CYCLES; REUSABLE CATALYST;

ALUMINA; AMINATION; AROMATIC COMPOUNDS; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; COPPER;

AMINES;

ALIPHATIC AMINE; ALUMINUM; AROMATIC AMINE; CHLORIDE; COPPER; HETEROCYCLIC AMINE;

ALKYLATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; FILTRATION;

EID: 69749096440     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216890     Document Type: Article

References (38)

1. (a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
2. (b) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623.
3. (c) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415.
4. (d) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892.
5. (a) Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
6. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
7. (c) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
8. (d) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
9. (a) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Eur. J. Org. Chem. 2004, 69, 695.
10. (b) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
11. (a) Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Synthesis 2005, 496.
12. (b) Ma, D.; Cai, Q. Synlett 2004, 128.
13. (a) Ohmori, J.; Shimizu-Sasamata, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1996, 39, 3971.
14. (b) Antonini, I.; Cristalli, G.; Franchetti, P.; Grifantini, M.; Martelli, S. Synthesis 1983, 47.
15. (a) Lindley, J. Tetrahedron 1984, 40, 1433.
16. (b) Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
17. (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
18. (a) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
19. (b) Zang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
20. (a) Lu, Z.; Twieg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 6289.
21. (b) Lu, Z.; Twieg, R. J. Tetrahedron 2005, 61, 903.
22. (c) Zang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.
23. (a) Xu, L.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2005, 61, 6553.
24. (b) Zhu, D.; Wang, R.; Xu, J.; Mao, J.; Xu, L.; Wu, F.; Wan, B. J. Mol. Catal. A: Chem. 2006, 256, 256.
25. (c) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
26. Sels, F.; De Vos, D. E.; Jacobs, P. A. Catal. Rev. 2001, 43, 443.
27. Choudary, B. M.; Sridhar, Ch.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948.
28. Kantam, M. L.; Purna Chandar Rao, P.; Choudary, B. M.; Sudarshan Reddy, R. Synlett 2006, 2195.
29. Likhar, P. R.; Arundhathi, R.; Kantam, M. L. Tetrahedron Lett. 2007, 48, 3911.
30. (a) Koelsch, C. F.; Carney, J. J. O. J. Am. Chem. Soc. 1950, 72, 2285.
31. (b) Randell, K. D.; Johnston, B. D.; Green, D. F.; Pinto, B. M. J. Org. Chem. 2000, 65, 220.
32. (c) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
33. (d) Xie, X.; Zhang, T. Y.; Zhang, Z. J. Org. Chem. 2006, 71, 6522.
34. (e) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron 1995, 51, 7959.
35. (f) Heutling, A.; Pohlki, F.; Doye, S. Chem. Eur. J. 2004, 10, 3059.
36. (a) Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413.
37. (b) Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672.
38. (c) Pearson, A. J.; Gelormini, A. M. J. Org. Chem. 1994, 59, 4561.