Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2505-2508

  Huang, Qinhua ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; NAPHTHALENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; METHODOLOGY; SYNTHESIS;

ALKYNES; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; CYCLIZATION; NAPHTHALENES; PALLADIUM;

EID: 0038707370     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026128y     Document Type: Article

References (29)

1. For reviews, see: (a) Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
2. (b) Larock, R. C. Palladium-Catalyzed Annulation. In Perspectives in Organopalladium Chemistry for the XXI Century; Tsuji, J., Ed.; Elsevier Press: Lausanne, Switzerland, 1999; pp 111-124.
3. (c) Larock, R. C. Pure Appl. Chem. 1999, 71, 1435.
4. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
5. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
6. (a) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
7. (b) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412.
8. Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
9. Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770.
10. Larock, R. C.; Han, X.; Doty, M. J. Tetrahedron Lett. 1998, 39, 5713.
11. Larock, R. C.; Doty, M. J.; Cacchi, S. J. J. Org. Chem. 1993, 58, 4579.
12. (a) Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306.
13. (b) Roesch, K. R.; Zhang, H.; Larock, R. C. J. Org. Chem. 2001, 66, 8042.
14. Zhang, H.; Larock, R. C. Org. Lett. 2001, 3, 3083.
15. (a) Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536.
16. (b) Larock, R. C.; Tian, Q. J. Org. Chem. 1998, 63, 2002.
17. (a) Whiting, D. A. Nat. Prod. Rep. 1985, 2, 191.
18. (b) Ward, R. S. Nat. Prod. Rep. 1995, 12, 183.
19. (c) Eich, E.; Pertz, H.; Kaloga, M.; Schulz, J.; Fesen, M. R.; Mazumder, A.; Pommier, Y. J. Med. Chem. 1996, 39, 86.
20. (d) Smyth, M. S.; Stefanova, I.; Horak, I. D.; Burke, T. R., Jr. J. Med. Chem. 1993, 36, 3015.
21. (e) Zhao, H.; Neamati, N.; Mazumder, A.; Sunder, S.; Pommier, Y.; Burke, T. R., Jr. J. Med. Chem. 1997, 40, 1186.
22. (f) Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamto, Y.; Takahashi, M.; Kotera, J.; Ikeo, T. J. Med. Chem. 1999, 42, 1293.
23. (a) Charlton, J. L.; Oleschuk, C. J.; Chee, G.-L. J. Org. Chem. 1996, 61, 3452.
24. (b) Katritzky, A. R.; Zhang, G.; Xie. L. J. Org. Chem. 1997, 62, 721.
25. (c) Nishii, Y.; Yoshida, T.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 7195.
26. (d) Cotelle, P.; Catteau, J.-P. Tetrahedron Lett. 1997, 38, 2969.
27. (e) de Koning, C. B.; Michael, J. P.; Rousseau, A. L. J. Chem. Soc., Perkin Trans. 1 2000, 787.
28. (f) Kao, C-L.; Yen, S. Y.; Chern, J.-W. Tetrahedron Lett. 2000, 41, 2207.
29. (g) Kajikawa, S.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 2001, 42, 3351.