An improved Ullmann-Ukita-Buchwald-Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides

Tetrahedron

Volumn 61, Issue 11, 2005, Pages 2931-2939

  Wang, Po Shih ^a   Liang, Chih Kai ^a   Leung, Man Kit ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

2 Pyridones; C N coupling; Copper reagents; Toluene

Indexed keywords

COPPER DERIVATIVE; HALIDE; PYRIDONE DERIVATIVE; TOLUENE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; PRIORITY JOURNAL;

EID: 14344256681     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.063     Document Type: Article

References (51)

1. For reviews, see (a) S.McN. Sieburth M. Harmata The Inter- and Intramolecular [4+4] Photocycloaddition of 2-Pyridones and Its Application to Natural Product Synthesis Advances in Cycloaddition Vol. 5 1999 JAI Greenwich, CT 85
2. G. Mehta, and V. Singh Chem. Rev. 99 1999 881 930
3. J.A. Joule, K. Mills, and G.F. Smith Heterocyclic Chemistry 3rd ed. 1995 Chapman and Hall London pp 87-93
4. M. Kuzuya, and A. Noguchi Trends Org. Chem. 2 1991 73
5. S. Kohmoto, T. Noguchi, H. Masu, K. Kishikawa, M. Yamamoto, and K. Yamaguchi Org. Lett. 6 2004 683 685
6. K. Tanaka, T. Fujiwara, and Z. Urbanczyk-Lipkowska Org. Lett. 4 2002 3255 3257
7. M. Zhu, Z. Qiu, G.P. Hiel, S. Sieburth, and McN J. Org. Chem. 67 2002 3487 3493
8. T.A. Ader, C.A. Champey, L.V. Kuznetsova, T. Li, Y.-H. Lim, D. Rucando, and S.McN. Sieburth Org. Lett. 3 2001 2165 2167
9. Y.-g. Lee, K.F. McGee Jr., J. Chen, D. Rucando, and S.McN. Sieburth J. Org. Chem. 65 2000 6676 6681
10. S.McN. Sieburth, K.F. McGee Jr., F. Zhang, and Y.J. Chen Org. Chem. 65 2000 1972 1977
11. T. Bach, H. Bergmann, and K. Harms Org. Lett. 3 2001 601 603
12. E. Bossharth, P. Desbordes, N. Monteiro, and G. Balme Org. Lett. 5 2003 2441 2444
13. Margolin, S. B. US patents: 5,518,729 1996, 5,716,632, 1998; 5,962,478 1999, 6,090,822 2000; 6,114,353 2000.
14. K. Itami, D. Yamazaki, and J.-i. Yoshida Org. Lett. 5 2003 2161 2164
15. Y. Yamamoto, H. Takagishi, and K. Itoh Org. Lett. 3 2001 2117 2119
16. B.T. O'Neill, D. Yohannes, M.W. Bundesmann, and E.P. Arnold Org. Lett. 2 2000 4201 4204
17. M. Moreno-Mañas, R. Pleixats, and M. Villarroya Tetrahedron 49 1993 1457 1464
18. A.R. Katritzky, and S. Sengupta Tetrahedron Lett. 28 1987 5419 5422
19. M. Sugahara, Y. Moritani, T. Kuroda, K. Kondo, H. Shimadzu, and T. Ukita Chem. Pharm. Bull. 48 2000 589 591
20. M. Sugahara, and T. Ukita Chem. Pharm. Bull. 45 1997 719 721
21. C.S. Li, and D.D. Dixon Tetrahedron Lett. 45 2004 4257 4260
22. B. Renger Synthesis 1985 856 860
23. P.Y.S. Lam, G. Vincent, D. Bonne, and C.G. Clark Tetrahedron Lett. 43 2002 3091 3094
24. Early copper catalyzed C-N bond coupling was reported by H. Gilman, and L.O. Moore J. Am. Chem. Soc. 79 1957 3485 3487
25. J.P. Wolfe, S. Wagaw, J.-F. Marcoux, and S.L. Buchwald Acc. Chem. Res. 31 1998 805 818
26. J.F. Hartwig Angew. Chem., Int. Ed. 37 1998 2046 2067
27. F.Y. Kwong, and S.L. Buchwald Org. Lett. 5 2003 793 796
28. F.Y. Kwong, A. Klapars, and S.L. Buchwald Org. Lett. 4 2002 581 584
29. R. Gujadhur, D. Venkataraman, and J.T. Kintigh Tetrahedron Lett. 42 2001 4791 4793
30. R.K. Gujadhur, C.G. Bates, and D. Venkataraman Org. Lett. 3 2001 4315 4317
31. H.B. Goodbrand, and N.-X. Hu J. Org. Chem. 64 1999 670 674
32. A.A. Kelkar, N.M. Patil, and R.V. Chaudhari Tetrahedron Lett. 43 2002 7143 7146
33. F. Lang, D. Zewge, I.N. Houpis, and R.P. Volante Tetrahedron Lett. 42 2001 3251 3254
34. A. Klapars, J.C. Antilla, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7727 7729
35. A. Klapars, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 7421 7428
36. J.C. Antilla, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 11684 11688
37. S.-K. Kang, D.-H. Kim, and J.-N. Park Synlett 2002 427 430
38. A. Kiyomori, J.-F. Marcoux, and S.L. Buchwald Tetrahedron Lett. 40 1999 2657 2660
39. M. Wolter, A. Klapars, and S.L. Buchwald Org. Lett. 3 2001 3803 3805
40. While DMF is a teratogen, dioxane is a carcinogen suspect agent.
41. M.-k. Leung, A.B. Mandal, C.-C. Wang, G.-H. Lee, S.-M. Peng, H.-L. Cheng, G.-R. Her, I. Chao, H.-F. Lu, Y.-C. Sun, M.-Y. Shiao, and P.-T. Chou J. Am. Chem. Soc. 124 2002 4287 4297
42. C.-H. Chien, M.-k. Leung, J.-K. Su, G.-H. Li, Y.-H. Liu, and Y. Wang J. Org. Chem. 69 2004 1866 1871
43. Substitution of the bromo group by sterically less hindered alkoxides has been previous reported by several teams. For reference, see K. Tomioka, Y. Shinmi, K. Shiina, M. Nakajima, and K. Koga Chem. Pharm. Bull. 38 1990 2133 2135
44. E.C. Taylor, K.A. Harrison, and J.B. Rampal J. Org. Chem. 51 1986 101 102
45. B.M. Bain, and J.E. Saxton J. Chem. Soc. 1961 5216 5223
46. M. Sugahara, and T. Ukita Chem. Pharm. Bull. 45 1997 719 721
47. D.D.M. Werner, T. Christos, C. Bertram, G. Johannes, and B. Christopher Eur. Pattern 57 2002 236
48. M. Masakatsu, and W. Nobuko JP Pattern 81 2003 977
49. D.S. Jane, J.H. Hutchinson, A.W. Shaw, S.L. Graham, and T.M. Ciccarone Eur. Pattern 17 1999 777
50. V.V. Kane, W. Harvey, and S.D. Levine J. Heterocyclic Chem. 13 1976 673 674
51. R. Alicja, S. Alicja, and B.-D. Halina Acta Polon. Pharm. 20 1963 155 167