Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling

Organic Letters

Volumn 12, Issue 9, 2010, Pages 2000-2003

  Jia, Wei ^a   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMIDE; COPPER; PROPIOLIC ACID; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKYNES; AMIDES; CATALYSIS; COPPER; OXIDATION-REDUCTION; PROPIONATES;

EID: 77951780267     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1004615     Document Type: Article

References (77)

1. For some reviews, see
2. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
3. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534
4. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
5. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337
6. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428
7. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
8. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874
9. For some reviews, see
10. Tracey, M. R.; Hsung, R. P.; Antoline, J.; Kurtz, K. C. M.; Shen, L.; Slafer, B. W.; Zhang, Y. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Weinreb, S. M., Ed.; Thieme: Stuttgart, Germany, 2005; Vol. 21, p 387.
11. Witulski, B.; Alayrac, C. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; de Meijere, A., Ed.; Thieme: Stuttgart, Germany, 2005; Vol. 24, p 1031.
12. Hsung, R. P.; Mulder, J. A.; Kurtz, K. C. M. Synlett 2003, 1379
13. Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455
14. Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575
15. For some recent examples, see
16. Gourdet, B.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 3802
17. Dooleweerdt, K.; Ruhland, T.; Skrydstrup, T. Org. Lett. 2009, 11, 221
18. Zhang, Y.; DeKorver, K. A.; Lohse, A. G.; Zhang, Y.-S.; Huang, J.; Hsung, R. P. Org. Lett. 2009, 11, 899
19. Alayrac, C.; Schollmeyer, D.; Witulski, B. Chem. Commun. 2009, 1464
20. Garcia, P.; Moulin, S.; Miclo, Y.; Leboeuf, D.; Gandon, V.; Aubert, C.; Malacria, M. Chem.- Eur. J. 2009, 15, 2129
21. Sato, A.; Yorimitsu, H.; Oshima, K. Synlett 2009, 28
22. Zhang, X.; Hsung, R. P.; Li, H.; Zhang, Y.; Johnson, W. L.; Figueroa, R. Org. Lett. 2008, 10, 3477
23. Kim, J. Y.; Kim, S. H.; Chang, S. Tetrahedron Lett. 2008, 49, 1745
24. Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361
25. Oppilliart, S.; Mousseau, G.; Zhang, L.; Jia, G.; Thuéry, P.; Rousseau, B.; Cintrat, J.-C. Tetrahedron 2007, 63, 8094
26. Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586
27. Couty, S.; Meyer, C.; Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726
28. Das, J. P.; Chechik, H.; Marek, I. Nat. Chem. 2009, 1, 128
29. Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965
30. Witulski, B.; Gössmann, M. Synlett 2000, 1793
31. Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272
32. Witulski, B.; Gössmann, M. Chem. Commun. 1999, 1879
33. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489
34. Yao, B.; Liang, Z.; Niu, T.; Zhang, Y. J. Org. Chem. 2009, 74, 4630
35. Dooleweerdt, K.; Birkedal, H.; Ruhland, T.; Skrydstrup, T. J. Org. Chem. 2008, 73, 9447
36. Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170
37. Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151
38. Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368
39. Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011
40. Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381
41. Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833
42. For a review, see
43. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632
44. For some reviews, see
45. Goossen, L. J.; Rodríguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47, 3100
46. Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373
47. You, S.-L.; Dai, L.-X. Angew. Chem., Int. Ed. 2006, 45, 5246
48. Tunge, J. A.; Burger, E. Eur. J. Org. Chem. 2005, 1715
49. For some selected examples, see
50. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
51. Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852
52. Lou, S.; Westbrook, J. A.; Schaus, S. E. J. Am. Chem. Soc. 2004, 126, 11440
53. Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323
54. Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510
55. Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
56. Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002
57. Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350
58. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138
59. He, H.; Zheng, X.-J.; Li, Y.; Dai, L.-X.; You, S.-L. Org. Lett. 2007, 9, 4339
60. Goossen, L. J.; Zimmermann, B.; Knauber, T. Angew. Chem., Int. Ed. 2008, 47, 7103
61. Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043
62. Goossen, L. J.; Rodríguez, N.; Linder, C. J. Am. Chem. Soc. 2008, 130, 15248
63. Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118
64. Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945
65. Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403
66. Yoshino, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 7494
67. Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738
68. Wang, C.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 4194
69. Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem., Int. Ed. 2009, 48, 792
70. Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 9350
71. For some examples with air as oxidant, see
72. Chen, X.; Zhu, H.-Y.; Zhao, J.-C.; Zheng, Z.-F.; Gao, X.-P. Angew. Chem., Int. Ed. 2008, 47, 5353
73. Kondo, J.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2003, 42, 825
74. Dioxygen as an ideal oxidant has offered attractive industrial prospects in terms of green and sustainable chemistry, for some reviews see: Costas, M.; Mehn, M. P.; Jensen, M. P., Jr.; Que, L. Chem. Rev. 2004, 104, 939
75. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400
76. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329
77. Popp, B. V.; Stahl, S. S. Top. Organomet. Chem. 2007, 22, 149