Copper-catalyzed N-arylation reaction of 2-azabicyclo[2.2.1]hept-5-en-3-one with arylboronic acids under microwave irradiation

Heterocycles

Volumn 76, Issue 1, 2008, Pages 133-136

  Abe, Takumi ^a   Takeda, Hiroyuki ^a   Yamada, Koji ^a   Ishikura, Minoru ^a  

^a HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 60049091085     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-07-S(N)6     Document Type: Article

References (22)

1. L. A. Agrofoglio, I. Gillaizeau, and Y. Sato, Chem. Rev., 2003, 103, 1875.
2. M. S. Raasch, J. Org. Chem., 1975, 40, 161;
3. M. Legraverend, E. Bisagni, and C. Huel, J. Heterocycl. Chem., 1989, 26, 1881;
4. M. B. Hursthouse, K. M. A. Malik, D. E. Hibbs, S. M. Roberts, A. J. H. Seago, V. Sik, and R. Storte, J. Chem. Soc., Perkin Trans. 1, 1995, 2419;
5. M. F. Schneider, N. Lucas, J. Velder, and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 257;
6. O. Arjona, A. G. Csákÿ, R. Medel, and J. Plumet, J. Org. Chem., 2002, 67, 1380;
7. N. Katagiri, Y. Yamatoya, and M. Ishikura, Tetrahedron Lett., 1999, 40, 9069;
8. M. Ishikura, A. Murakami, and N. Katagiri, Org. Biomol. Chem., 2003, 1, 452;
9. M. Ishikura, K. Matsumoto, and A. Murakami, Heterocycles, 2004, 64, 241;
10. M. Ishikura, M. Hasunuma, K. Yamada, and R. Yanada, Heterocycles, 2006, 68, 2253.
11. C. F. Palmer, K. P. Parry, S. M. Roberts, and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1992, 1021;
12. C. F. Palmer and R. McCague, J. Chem. Soc., Perkin Trans. 1, 1998, 2977.
13. M. Ishikura, M. Saijo, and A. Hino, Heterocycles, 2002, 57, 241;
14. M. Ishikura, M. Hasunuma, and K. Yanada, Heterocycles, 2005, 65, 2587.
15. T. Abe, H. Takeda, Y. Takahashi, and M. Ishikura, unpublished data.
16. S. V. Ley and A. W. Thomas, Angew. Chem. Int. Ed., 2003, 42, 5400.
17. D. M. T. Chan, Tetrahedron Lett., 1996, 37, 9013;
18. D. M. T. Chan, K. L. Monaco, R. P. Wang, and M. P. Winters, Tetrahedron Lett., 1998, 39, 2933.
19. D. A. Evans, J. L. Katz, and T. R. West, Tetrahedron Lett., 1998, 39, 2937;
20. P. Y. S. Lam, G. Vincent, C. G. Clark, S. Deudon, and P. K. Jadhav, Tetrahedron Lett., 2001, 42, 3415.
21. Microwave (MW) irradiation (300 W) was carried out in a glass tube using a Green-Motif I (IMCR-25003) monomode microwave reactor (IDX Corporation).
22. 11NO: 185.0841. Found: 185.0845.