A versatile copper-catalyzed coupling reaction of pyridin-2(1H)-ones with aryl halides

Tetrahedron Letters

Volumn 47, Issue 44, 2006, Pages 7677-7680

  Filipski, Kevin J ^a   Kohrt, Jeffrey T ^a   Casimiro Garcia, Agustin ^a   Van Huis, Chad A ^a   Dudley, Danette A ^a   Cody, Wayne L ^a   Bigge, Christopher F ^a   Desiraju, Shrilakshmi ^b   Sun, Shaoyi ^b   Maiti, Samarendra N ^b   Jaber, Mohamad R ^c   Edmunds, Jeremy J ^a  

^a PFIZER INC   (United States)

^b NAEJA Pharmaceutical Inc   (Canada)

^c PharmAgra Labs   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 QUINOLINOL; COPPER; HALIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; SYNTHESIS;

EID: 33748954624     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.112     Document Type: Article

References (25)

1. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
2. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428-2439
3. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
4. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421-7428
5. Charles M.D., Schultz P., and Buchwald S.L. Org. Lett. 7 (2005) 3965-3968
6. Tundel R.E., Anderson K.W., and Buchwald S.L. J. Org. Chem. 71 (2006) 430-433
7. Shafir A., and Buchwald S.L. J. Am. Chem. Soc. 128 (2006) 8742-8743
8. Renger B. Synthesis (1985) 856-860
9. Sugahara M., and Ukita T. Chem. Pharm. Bull. 45 (1997) 719-721
10. Lam P.Y.S., Clark C.G., Saubern S., Adams J., Averill K.M., Chan D.M.T., and Combs A. Synlett 5 (2000) 674-676
11. Lam P.Y.S., Vincent G., Clark C.G., Deudon S., and Jadhav P.K. Tetrahedron Lett. 42 (2001) 3415-3418
12. Mederski W.W.K.R., Lefort M., Germann M., and Kux D. Tetrahedron 55 (1999) 12757-12770
13. Lam P.Y.S., Vincent G., Bonne D., and Clark C.G. Tetrahedron Lett. 43 (2002) 3091-3094
14. Li C.S., and Dixon D.D. Tetrahedron Lett. 45 (2004) 4257-4260
15. Wang P.-S., Liang C.-K., and Leung M.-k. Tetrahedron 61 (2005) 2931-2939
16. Cristau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Chem. Eur. J. 10 (2004) 5607-5622
17. Ikegai K., Nagata Y., and Mukaiyama T. Bull. Chem. Soc. Jpn. 79 (2006) 761-767
18. Hu T., and Li C. Org. Lett. 7 (2005) 2035-2038
19. Kwong F.Y., Klapars A., and Buchwald S.L. Org. Lett. 4 (2002) 581-584
20. Fagan P.J., Hauptman E., Shapiro R., and Casalnuovo A. J. Am. Chem. Soc. 122 (2000) 5043-5051
21. +).
22. Zhou, J. C.; Confalone, P. N.; Li, H.; Oh, L. M.; Rossano, L. T.; Clark, C. G.; Teleha, C. A. WO 0208199.
23. Ukita reported a 0% yield for a similar reaction of iodobenzene coupling to 2-hydroxyquinoline using the ligand-free conditions.
24. Ukita reported a 0% yield for a similar reaction of iodobenzene coupling to 4(3H)-pyrimidone using the ligand-free conditions.
25. 1H NMR and MS data.