Microwave-assisted efficient copper-promoted N-arylation of amines with arylboronic acids

Journal of Combinatorial Chemistry

Volumn 10, Issue 3, 2008, Pages 358-360

  Chen, Shiyu ^a,b   Huang, He ^a   Liu, Xuejun ^b   Shen, Jingkang ^a,b   Jiang, Hualiang ^a,c   Liu, Hong ^a  

^a Shanghai Jiao Tong University Affiliated Sixth People s Hospital   (China)

^b Central Research Institute of Shanghai Pharmaceutical Group   (China)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BORONIC ACID DERIVATIVE; COPPER ACETATE; ORGANOMETALLIC COMPOUND;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; MICROWAVE RADIATION; RADIATION EXPOSURE; STEREOISOMERISM; SYNTHESIS;

AMINATION; AMINES; BORONIC ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MICROWAVES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 45149126071     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc8000053     Document Type: Article

References (45)

1. For reviews and recent examples, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
2. (b) Chegaev, K.; Lazzarato, L.; Tosco, P.; Cena, C.; Marini, E.; Rolando, B.; Carrupt, P. A.; Fruttero, R.; Gasco, A. J. Med. Chem. 2007, 50, 1449.
3. (c) Wiglenda, T.; Gust, R. J. Med. Chem. 2007, 50, 1475.
4. (d) Davey, D. D.; Adler, M.; Arnaiz, D.; Eagen, K.; Erickson, S.; Guilford, W.; Kenrick, M.; Morrissey, M. M.; Ohlmeyer, M.; Pan, G.; Paradkar, V. M.; Parkinson, J.; Polokoff, M.; Saionz, K.; Santos, C.; Subramanyam, B.; Vergona, R.; Wei, R. G.; Whitlow, M.; Ye, B.; Zhao, Z. S.; Devlin, J. J.; Phillips, G. J. Med. Chem. 2007, 50, 1146.
5. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
6. (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691.
7. For the efforts on copper catalyzed arylation of amines, see: (a) Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem., Int. Ed. 2007, 46, 934.
8. (b) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
9. (c) Rao, H. H.; Jin, Y.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Chem.-Eur. J. 2006, 12, 3636.
10. (d) de Lange, B.; Lambers-Verstappen, M. H.; van de Vondervoort, L. S.; Sereinig, N.; de Rijk, R.; de Vries, A. H. M.; de Vries, J. G. Synlett 2006, 3105.
11. (e) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
12. (f) Liu, L. B.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135.
13. (g) Kuil, M.; Bekedam, E. K.; Visser, G. M.; van den Hoogenband, A.; Terpstra, J. W.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Tetrahedron Lett. 2005, 46, 2405.
14. (h) Jerphagnon, T.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. Org. Lett. 2005, 7, 5241.
15. (i) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
16. (j) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem.-Eur. J. 2004, 10, 5607.
17. (k) Ma, D. W.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
18. (l) Lv, X.; Wang, Z. M.; Bao, W. L. Tetrahedron 2006, 62, 4756.
19. For the efforts on palladium catalyzed arylation of amines, see: (m) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
20. (n) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
21. (o) Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523.
22. (p) Barluenga, J.; Aznar, F.; Valdes, C. Angew. Chem., Int. Ed. 2004, 43, 343.
23. (q) Sturmer, R. Angew. Chem., Int. Ed. 1999, 38, 3307.
24. For Chan-Lam-modified Ullmann coupling reaction, see: Chan, D. M. T.; Monaco Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
25. (b) 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.
26. (c) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623.
27. (d) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Averill, K. M.; Chan, D. M. T.; Combs, A. Synlett 2000, 674.
28. (e) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927.
29. (f) Chan, D. M. T.; Monaco, K. L.; Li, R. H.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863.
30. (g) Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691.
31. (h) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415.
32. For the efforts on arylation of amines using boronic acids, see: (a) Kantam, M. L.; Venkanna, G. T.; Sridhar, C.; Sreedhar, B.; Choudary, B. M. J. Org. Chem. 2006, 71, 9522.
33. (b) Singh, B. K.; Appukkuttan, P.; Claerhout, S.; Parmar, V. S.; Van der Eycken, E. Org. Lett. 2006, 8, 1863.
34. (c) Das, P.; Basu, B. Synth. Commun. 2004, 34, 2177.
35. (d) Chiang, G. C. H.; Olsson, T. Org. Lett. 2004, 6, 3079.
36. (e) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397.
37. (f) Combs, A. P.; Tadesse, S.; Rafalski, M.; Haque, T. S.; Lam, P. Y. S. J. Comb. Chem. 2002, 4, 179.
38. (g) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892.
39. (h) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699.
40. (i) Collman, J. P.; Zhong, M.; Zeng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528.
41. For recent efforts on microwave-assistted reactions, please see: (a) Sun, L. P.; Dai, W. M. Angew. Chem., Int. Ed. 2006, 45, 7255.
42. (b) Shore, G.; Morin, S.; Organ, M. G. Angew. Chem., Int. Ed. 2006, 45, 2761.
43. (c) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
44. (d) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
45. (e) Huang, H.; Liu, H.; Chen, K. X.; Jiang, H. L. J. Comb. Chem. 2007, 9, 197.