Highly functional group tolerance in copper-catalyzed N-arylation of nitrogen-containing heterocycles under mild conditions

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 2200-2202

  Zhu, Liangbo ^a   Li, Gaocan ^a   Luo, Liang ^a   Guo, Peng ^a   Lan, Jingbo ^a   You, Jingsong ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMO SELECTIVITIES; N-ARYLATION; N-ARYLATION REACTIONS; NITROGEN-CONTAINING HETEROCYCLES;

AROMATIC COMPOUNDS;

FUNCTIONAL GROUPS;

COPPER; IMIDAZOLE DERIVATIVE; NITROGEN;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; METAL TOLERANCE; STEREOCHEMISTRY; TEMPERATURE;

CATALYSIS; COPPER; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM; TEMPERATURE;

EID: 64249097478     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802669b     Document Type: Article

References (56)

1. For reviews of transition-metal-catalyzed reactions, see: (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
2. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
3. (c) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.,; de MeijereA. Eds.;, Wiley-VCH: Weinheim, Germany. 2004.
4. (d) Hartwig, J. F. Synlett 2006, 1283.
5. (e) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
6. For reviews of copper-catalyzed reactions, see: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
7. (b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
8. Two breakthroughs from the research groups of Taillefer and Buchwald: (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
9. (b) Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. Fr 2833947-WO 0353225 (Pr. Nb. Fr 2001 16547), 2001.
10. Foe selected copper-catalyzed reactions, see: (a) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc 2002, 124, 11684.
11. (b) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
12. (c) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
13. (d) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer. M. Eur. J. Org. Chem. 2004, 695.
14. (e) Cristau, H. J.; Cellier, P. P.; Hamada, S.; Spindler, J. F.; Taillefer, M. Org. Lett. 2004, 6, 913.
15. (f) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
16. (g) Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur. J. 2006, 12, 3636.
17. (h) Guo, X.; Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2006, 348, 2197.
18. (i) Ma, H.; Jiang, X. J. Org. Chem. 2007, 72, 8943.
19. (j) Xia, N.; Taillefer, M. Chem. Eur. J. 2008, 14, 6037.
20. Selected examples in the absence of additional ligand: (a) Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am, Chem. Soc. 2005, 127, 9948.
21. (b) Correa, A.; Bolm, C. Adv. Synth. Catal. 2007, 349, 2673.
22. (c) Taillefer, M.; Xia, N.; Oualli, A. Angew. Chem. Int. Ed. 2007, 46, 934.
23. (d) Zhao, Y.; Wang, Y.; Sun, H.; Li, L.; Zhang, H. Chem. Commun. 2007, 3186.
24. (e) Rout, L.; Sen, T. K.; Punniyamurthy, T. Angew. Chem., Int. Ed. 2007, 46, 5583.
25. (f) Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. J. Org. Chem. 2008, 73, 5625.
26. (g) Zhu, R.; Xing, L.; Wang, X.; Cheng, C.; Su, D.; Hu, Y. Adv. Synth. Catal. 2008, 350, 1253.
27. (h) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 43, 7143.
28. The coupling of aryl iodides: (a) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
29. (b) Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2007, 46, 8862.
30. (c) Bistri. O.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 586.
31. (d) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
32. (e) Carril, M.; Correa, A.; Bolm, C. Angew. Chem, Int. Ed. 2008, 47, 4862.
33. Selected copper-catalyzed reactions under mild conditions: (a) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
34. (b) Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490.
35. (c) Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
36. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
37. (b) Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853.
38. (a) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096.
39. (b) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703.
40. (a) Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135.
41. (b) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
42. (c) Altman. R. A.; Koval, E. D.; Buchwald. S. L. J. Org. Chem. 2007, 72, 6190.
43. (d) Zhu, L.; Guo, P.; Li, G.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535.
44. (e) Zhu, L.; Cheng, L.; Zhang, Y.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 2737.
45. (f) Chen, W.; Zhang, Y.; Zhu, L.; Lan, J.; Xie, R.; You, J. J. Am. Chem. Soc. 2007, 129, 13879.
46. (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 315.
47. (b) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727.
48. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
49. (d) Li, J.; Li, J.; Wang, D.; Pi, S.; Xie, Y.; Zhang, M.; Hu, X. J. Org. Chem. 2007, 72, 2053.
50. (e) Tang, B.; Wang, F.; Li, T.; Xie, Y.; Zhang, M. J. Org. Chem. 2007, 72, 6294.
51. (a) Brakta, M.; Murthy, D.; Ellis, L'O.; Phadtare, S. Bioorg. Med. Chem. Lett. 2002, 12, 1489.
52. (b) Mano, T.; Stevens, R. W.; Ando, K.; Nakao, K.; Okumura, Y.; Sakakibara, M.; Okumura, T.; Tamura, T.; Miyamoto, K. Bioorg. Med. Chem, 2003, 11, 3879.
53. (c) Ueno, Y.; Kato, T.; Sato, K.; Ito, Y.; Yoshida, M.; Inoue, T.; Shibata, A.; Ebihara, M.; Kitade. Y. J Org. Chem. 2005, 70, 7925.
54. (a) Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973.
55. (b) Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Alikarami, M. Synlett 2005, 1101.
56. Before the N-arylation of imidazole with aryl halide containing the aldehyde moiety, the forrnyl group needed to be protected as ketal: Velaparthi, U.; Wittman, M.; Liu, P.; Stoffan, K.; Zimmermann, K.; Sang, X.; Carboni, J.; Li, A.; Attar, R.; Gottardis, M.; Greer, A.; Chang, C.Y. Y.; Jacobsen, B. L.; Sack, J. S.; Sun, Y.; Langley, D. R.; Balasubramanian. B.; Vyas, D. Bioorg. Med. Chem. Lett. 2007, 17, 2317.