Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions

Synthesis

Volumn , Issue 3, 2005, Pages 496-499

  Cai, Qian ^a   Zhu, Wei ^b   Zhang, Hui ^b   Zhang, Yongda ^b   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

Amino acids; Aryl amines; Aryl halides; Coupling reaction

Indexed keywords

AMINES; AMINO ACIDS; CATALYSIS; COPPER COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ARYL AMINES; COUPLING REACTIONS; N-ARYLIMIDAZOLES; N-ARYLPYRAZOLES;

AROMATIC COMPOUNDS;

AMINO ACID; AZIDE; BETA AMINO ACID; COPPER; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; IODINE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; ULLMANN TYPE COUPLING REACTION;

EID: 14644388821     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831196     Document Type: Article

References (30)

1. For a review, see: Lindley, J. Tetrahedron 1984, 40, 1433.
2. For reviews, see: (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
3. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
4. For reviews, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400.
5. (b) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
6. For some leading references, see: (a) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
7. (b) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
8. (c) Cristau, H.-J.; Cellier, P. P.; Hamada, S.; Spindler, J.-F.; Taillefer, M. Org. Lett. 2004, 6, 913.
9. (d) Han, C.; Shen, R.; Su, S.; Porco, J. A. Jr. Org. Lett. 2004, 6, 27.
10. (e) van Allen, D.; Venkataraman, D. J. Org. Chem. 2003, 68, 4590.
11. (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
12. (b) Also see:Ma, D.; Yao, J. Tetrahedron: Asymmetry 1996, 7, 3075.
13. Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
14. Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
15. Ma, D.; Cai, Q. Synlett 2004, 128.
16. Liu, Q.; Tor, Y. Org. Lett. 2003, 5, 2571; and references cited therein.
17. Zhu, W.; Ma, D. Chem. Commun. 2004, 888.
18. (a) Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173.
19. (b) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 110.
20. (c) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189.
21. (d) Reynolds, D. J.; Hermitage, S. A. Tetrahedron 2001, 57, 7765.
22. (e) Clement, J.-B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett 2001, 1423.
23. (f) Kamenecka, T. M.; Lanza, T. Jr.; de Laszlo, S. E.; Li, B.; McCauley, E. D.; Riper, G. V.; Egger, L. A.; Kidambi, U.; Mumford, R. A.; Tong, S.; MacCoss, M.; Schmidt, J. A.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2002, 12, 2205.
24. (g) Ma, D.; Xia, C.; Jiang, J.; Zhang, J.; Tang, W. J. Org. Chem. 2003, 68, 442.
25. (h) Reddy, T. J.; Chan, L.; Turcotte, N.; Proulx, M.; Pereira, O. Z.; Das, S. K.; Siddiqui, A.; Wang, W.; Poisson, C.; Yannopoulos, C. G.; Bilimoria, D.; L'Heureux, L.; Alaoui, H. M. A.; Nguyen-Ba, N. Bioorg. Med. Chem. Lett. 2003, 13, 3341.
26. (i) Greenspan, P. D.; Clark, K. L.; Cowen, S. D.; McQuire, L. W.; Tommasi, R. A.; Farley, D. L.; Quadros, E.; Coppa, D. E.; Du, Z.; Fang, Z.; Zhou, H.; Doughty, J.; Toscano, K. T.; Wigg, A. M.; Zhou, S. Bioorg. Med. Chem. Lett. 2003, 13, 4121.
27. (j) Ding, K.; Flippen-Anderson, J.; Deschamps, J. R.; Wang, S. Tetrahedron Lett. 2004, 45, 1027.
28. (k) Robichaud, J.; Bayly, C.; Oballa, R.; Prasit, P.; Mellon, C.; Falgueyret, J.-P.; Percival, M. D.; Wesolowski, G.; Rodan, S. B. Bioorg. Med. Chem. Lett. 2004, 14, 4291.
29. Polya, K. J. Chem. Soc. C 1970, 85.
30. Benin, V.; Kaszynski, P.; Radziszewski, J. G. J. Org. Chem. 2002, 67, 1354.