A general copper-catalyzed coupling of azoles with vinyl bromides

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6371-6373

  Liao, Qian ^a   Wang, Yuxing ^a   Zhang, Liyun ^a   Xi, Chanjuan ^a  

^a Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; COPPER;

CHEMICAL EQUATIONS; COPPER IODIDE; COPPER-CATALYZED COUPLINGS; DOUBLE BONDS; ETHYLENE DIAMINE; REACTION CONDITIONS; VINYL BROMIDES;

BROMINE COMPOUNDS;

BROMIDE; COPPER; PYRROLE DERIVATIVE; VINYL DERIVATIVE; ETHYLENEDIAMINE; ETHYLENEDIAMINE DERIVATIVE; LIGAND; VINYL BROMIDE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; GEOMETRY; METHODOLOGY; CHEMISTRY;

AZOLES; CATALYSIS; COPPER; ETHYLENEDIAMINES; LIGANDS; VINYL COMPOUNDS;

EID: 70349117722     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901105r     Document Type: Article

References (50)

1. Brustolin, F.; Castelvetro, V.; Ciardelli, F.; Rugger, G.; Colligiani, A. J. Polym. Sci., A: Polym. Chem. 2000, 39, 253-262.
2. (a) Ogata, M.; Matsumoto, H.; Shimizu, S.; Kida, S.; Shiro, M.; Tawara, K. J. Med. Chem. 1987, 30, 1348-1354.
3. (b) Hormi, O. E. O.; Hirvelä, L. Tetrahedron Lett. 1993, 34, 6463-6466.
4. (c) Gopal, D.; Rajagopalan, K. Tetrahedron Lett. 1987, 28, 5327-5330.
5. (a) Trofimov, B. A.; Tarasova, O. A.; Shemetova, M. A.; Afonin, A. V.; Klyba, L. V.; Baikalova, L. V.; Mikhaleva, A. I. Russ. J. Org. Chem. 2003, 39, 408-414.
6. (b) Trofimov, B. A.; Tarasova, O. A.; Mikhaleva, A. I.; Kalinina, N. A.; Sinegovskaya, L. M.; Henkelmann, J. Synthesis 2000, 1585-1590.
7. (c) Tzalis, D.; Koradin, C.; Knochel, P. Tetrahedron Lett. 1999, 40, 6193-6195.
8. (d) Bourgeois, P.; Lucrece, J.; Dunogues, J. J. Heterocycl. Chem. 1978, 15, 1543-1545.
9. Iddon, B.; Hartley, D. J. Tetrahedron Lett. 1997, 38, 4647-4650.
10. Maier, L.; Rist, G. Phosphorus Sulfur Relat. Elem. 1987, 32, 65-72.
11. Qian, H.; Huang, X. Synth. Commun. 2000, 30, 1413-1417.
12. Surprenant, S.; Chan, W. Y.; Berthelette, C. Org. Lett. 2003, 5, 4851-4854.
13. (a) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623-626.
14. (b) Dejli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973-1968
15. (c) Dehli, J. R.; Bolm, C. J. Org. Chem. 2004, 69, 8518-8520.
16. (d) Dehli, J. R.; Bolm, C. Adv. Synth. Catal. 2005, 347, 239-242.
17. For the latest examples of copper-catalyzed C-N bond formation, see: (a) Jiang, B.; Tian, H.; Huang, Z.-G.; Xu, M. Org. Lett. 2008, 10, 2737-2740.
18. (b) Fukudome, Y.; Naito, H.; Hata, T.; Urabe, H. J. Am. Chem. Soc. 2008, 130, 1820-1821.
19. (c) Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109-2112.
20. (d) Mao, J.; Hua, Q.; Guo, J.; Shi, D.; Ji, S. Synlett 2008, 2011-2016.
21. (e) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460.
22. (f) Lu, H.; Yuan, X.; Zhu, S.; Sun, C.; Li, C. J. Org. Chem. 2008, 73, 8665-8668.
23. (g) Martin, R.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 5521-5524.
24. (h) Cesati, R. R. I.; Dwyer, G.; Jones, R. C.; Hayes, M. P.; Yalamanchili, P.; Casebier, D. S. Org. Lett. 2007, 9, 5617-5620.
25. (i) Martin, R.; Larsen, C. H.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 3379-3382.
26. (j) He, G.; Wang, J.; Ma, D. Org. Lett. 2007, 9, 1367-1369.
27. (k) Yang, L.; Deng, G.; Wang, D.-X.; Huang, Z.-T.; Zhu, J.-P.; Wang, M.-X. Org. Lett. 2007, 9, 1387-1390.
28. (l) Rivero, M. R.; Buchwald, S. L. Org. Lett. 2007, 9, 973-976.
29. (m) Toumi, M.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2007, 46, 572-575.
30. (n) Yuan, X.; Xu, X.; Zhou, X.; Yuan, J.; Mai, L.; Li, Y. J. Org. Chem. 2007, 72, 1510-1513.
31. (o) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
32. (p) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
33. (q) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054-3131.
34. (r) Coste, A.; Karthikeyan, G.; François, C.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381-4385.
35. (s) Xia, N.; Taillefer,M. Angew. Chem., Int. Ed. 2009, 48, 337-339.
36. (t) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096-3099.
37. (u) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667-3669.
38. (v) Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672-674.
39. (a) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927-4931.
40. (b) Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109-2112.
41. (a) Dehli, J. R.; Bolm, C. J. Org. Chem. 2004, 69, 8518-8520.
42. (b) Wang, Z.; Bao, W.; Jiang, Y. Chem. Commun. 2005, 2849-2851.
43. (c) Ouali, A.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P.; Taillefer, M. J. Am. Chem. Soc. 2006, 128, 15990-15991.
44. (d) Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J.-F. Chem.;Eur. J. 2006, 12, 5301-5313.
45. (e) Bao, W.; Liu, Y.; Lv, X. Synthesis 2008, 1911-1917.
46. For representative examples, see: (a) Martín, R.; Rivero, M. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079-7082.
47. (b) Martín, R.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 5521-5524.
48. (c) Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78-88.
49. (d) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
50. (e) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.