CuI-catalyzed coupling reactions of aryl iodides with amides using L-proline and KF/Al2O3

Chinese Journal of Chemistry

Volumn 26, Issue 11, 2008, Pages 2120-2124

  Hosseinzadeh, Rahman ^a   Tajbakhsh, Mahmood ^a   Mohadjerani, Maryam ^a   Ghorbani, Elham ^a  

^a UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Amidation; Aryl iodide; Copper iodide; Coupling reaction; Potassium fluoride on alumina

Indexed keywords

EID: 57049186648     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200890379     Document Type: Article

References (43)

1. (a) Lindley, J. Tetrahedron 1984, 40, 1433.
2. (b) Finet, J. P.; Fedorov, A. Y.; Combes, S.; Boyer, G. Curr. Org. Chem. 2002, 6, 597.
3. (a) Vyshnyakova, T. P.; Golubeva, I. A.; Glebova, E. V. Russ. Chem. Rev. (Engl. Transl.) 1985, 54, 249.
4. (b) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.
5. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
6. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
7. (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
8. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
9. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
10. Lipshutz, B. H. Angew. Chem., Int. Ed. 2000, 39, 4492.
11. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
12. (b) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
13. (c) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
14. (d) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
15. (e) Okano, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 4987.
16. (f) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
17. (g) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
18. (h) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
19. (a) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
20. (b) Deng, W.; Wang, Y. F.; Zou, Y.; Liu, L.; Guo, Q. X. Tetrahedron Lett. 2004, 45, 2311.
21. (c) Deng, W.; Zhang, C.; Liu, M.; Zou, Y.; Liu, L.; Guo, Q. X. Chin. J. Chem. 2005, 23, 1241.
22. (d) Deng, W.; Liu, L.; Zhang, C.; Liu, M.; Guo, Q. X. Tetrahedron Lett. 2005, 46, 7295.
23. (e) Zheng, Y.; Du, X.; Bao, W. Tetrahedron Lett. 2006, 47, 1217.
24. (a) Yamawaki, J.; Ando, T.; Hanafusa, T. Chem. Lett. 1981, 1143.
25. (b) Alloum, B. A.; Villemin, D. Synth. Commun. 1989, 19, 2567.
26. (c) Yadav, V. K.; Kapoor, K. K. Tetrahedron 1996, 52, 3659.
27. (d) Kabalka, G. W.; Pagni, R. M.; Hair, C. M. Org. Lett. 1999, 1, 1423.
28. (e) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151.
29. (f) Blass, B. E. Tetrahedron 2002, 58, 9301.
30. Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Mehdinejad, H. Synlett 2004, 1517.
31. (a) Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Alikarami, M. Synlett 2005, 1101.
32. (b) Hosseinzadeh, R.; Tajbakhsh, M.; Alikarami, M. Tetrahedron Lett. 2006, 47, 5203.
33. (c) Hosseinzadeh, R.; Tajbakhsh, M.; Alikarami, M. Synlett 2006, 2124.
34. Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
35. (a) Lide, D. R. CRC Handbook of Chemistry and Physics, 79th ed., CRC Press, Cleveland, 1998.
36. (b) Faler, C. A.; Joullie, M. M. Tetrahedron Lett. 2006, 47, 7229.
37. (c) Babu, V. V. S.; Vasanthakumar, G. R.; Tantry, S. J. Tetrahedron Lett. 2005, 46, 4099.
38. (d) Gluzman, M. K.; Milner, R. S. Izzest. Vysshikh Ucheb. Zavedenil, Khim. i Khim. Tekhnol. 1960, 3, 305.
39. (e) Cauzzo, G.; Mazzucato, U.; Foffani, A. Atti Accad. Nazl. Lincei, Rend. Classe Sci. Fis. Mat. Nat. 1960, 29, 348.
40. (f) Buckingham, J.; Macdonald, F. Dictionary of Organic Compounds, 6th ed., Chapman and Hall, New York, 1996.
41. (g) Wu, X.; Hu, L. Tetrahedron Lett. 2005, 46, 8401.
42. (h) Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed., Longman, Harlow, 1989.
43. (i) Lopez-Alvarado, P.; Avendano, C.; Menendez, C. J. Org. Chem. 1996, 61, 5865.