Mild copper-mediated direct oxidative cross-coupling of 1,3,4-oxadiazoles with polyfluoroarenes by using dioxygen as oxidant

Chemistry - A European Journal

Volumn 19, Issue 10, 2013, Pages 3302-3305

  Zou, Liang Hua ^a   Mottweiler, Jakob ^a   Priebbenow, Daniel L ^a   Wang, Jun ^a   Stubenrauch, Jan Alexander ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

C H activation; copper; fluoroarenes; heterocycles; oxygen

Indexed keywords

1 ,3 ,4-OXADIAZOLES; C-H ACTIVATION; CROSS-COUPLINGS; DIOXYGENS; FLUOROARENES; HETEROCYCLES; MILD REACTION CONDITIONS;

ACETONITRILE; ACTIVATION ANALYSIS; CHEMICAL REACTIONS; FUNCTIONAL MATERIALS; OXYGEN;

COPPER;

EID: 84874433660     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204502     Document Type: Article

References (81)

1. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077
2. A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439
3. K. Godula, D. Sames, Science 2006, 312, 67
4. L.-C. Campeau, D. R. Stuart, K. Fagnon, Aldrichimica Acta 2007, 40, 35
5. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173
6. B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949
7. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
8. Angew. Chem. Int. Ed. 2009, 48, 5094
9. C.-J. Li, Acc. Chem. Res. 2009, 42, 335.
10. Y. Nakao, N. Kashihara, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 16170
11. R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593
12. S. A. Reed, A. R. Mazzotti, M. C. White, J. Am. Chem. Soc. 2009, 131, 11701
13. Y.-Z. Li, B.-J. Li, X.-Y. Lu, S. Lin, Z.-J. Shi, Angew. Chem. 2009, 121, 3875
14. Angew. Chem. Int. Ed. 2009, 48, 3817
15. M. Tobisu, I. Hyodo, N. Chatani, J. Am. Chem. Soc. 2009, 131, 12070
16. Y. Wei, J. Kan, M. Wang, W. Su, M. Hong, Org. Lett. 2009, 11, 3346; for recent reviews, see
17. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
18. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200
19. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
20. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
21. A. A. Kulkarni, O. Daugulis, Synthesis 2009, 4087
22. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
23. Angew. Chem. Int. Ed. 2009, 48, 9792
24. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677
25. T. Satoh, M. Miura, Synthesis 2010, 3395
26. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
27. J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170
28. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780
29. W. Han, A. R. Ofial, Synlett 2011, 1951
30. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
31. X. Bugaut, F. Glorius, Angew. Chem. 2011, 123, 7618
32. Angew. Chem. Int. Ed. 2011, 50, 7479
33. K. Hirano, M. Miura, Chem. Commun. 2012, 48, 10704.
34. Y. Kita, K. Morimoto, M. Ito, C. Ogawa, A. Goto, T. Dohi, J. Am. Chem. Soc. 2009, 131, 1668
35. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, J. You, J. Am. Chem. Soc. 2010, 132, 1822.
36. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172
37. D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072
38. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137.
39. K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 11904
40. B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131
41. Angew. Chem. Int. Ed. 2008, 47, 1115
42. G. Brasche, J. García-Fortanet, S. L. Buchwald, Org. Lett. 2008, 10, 2207
43. X. Zhao, C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2010, 132, 5837.
44. C.-Y. He, S. Fan, X. Zhang, J. Am. Chem. Soc. 2010, 132, 12850
45. Y. Wei, W. Su, J. Am. Chem. Soc. 2010, 132, 16377
46. H. Li, J. Liu, C.-L. Sun, B.-J. Li, Z.-J. Shi, Org. Lett. 2011, 13, 276.
47. Y. Li, J. Jin, W. Qian, W. Bao, Org. Biomol. Chem. 2010, 8, 326
48. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522
49. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2009, 131, 17052.
50. M. Kitahara, N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2011, 133, 2160
51. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2011, 133, 13577
52. Z. Mao, Z. Wang, Z. Xu, F. Huang, Z. Yu, R. Wang, Org. Lett. 2012, 14, 3854.
53. H. Chen, Z. Li, Y. Han, J. Agric. Food Chem. 2000, 48, 5312
54. X.-J. Zou, L.-H. Lai, G.-Y. Jin, Z.-X. Zhang, J. Agric. Food Chem. 2002, 50, 3757.
55. M. Vossoghi, T. Akbarzadeh, A. Fallah, M. R. Fazeli, H. Jamalifar, A. Shafiee, J. Sci., Islamic Repub. Iran 2005, 16, 146
56. A. A. El-Emam, O. A. Al-Deeb, M. Al-Omar, J. Lehmann, Bioorg. Med. Chem. 2004, 12, 5107
57. F. Macaev, G. Rusu, S. Pogrebnoi, A. Gudima, E. Stingaci, L. Vlad, N. Shvets, F. Kandemirli, A. Dimoglo, R. Reynolds, Bioorg. Med. Chem. 2005, 13, 4842
58. H. K. Misra, Arch. Pharm. 1983, 316, 487.
59. A. Zahn, C. Brotschi, C. J. Leumann, Chem. Eur. J. 2005, 11, 2125.
60. H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119
61. F. Babudri, G. M. Farinola, F. Naso, R. Ragni, Chem. Commun. 2007, 1003
62. M. L. Tang, A. D. Reichardt, N. Miyaki, R. M. Stoltenberg, Z. Bao, J. Am. Chem. Soc. 2008, 130, 6064
63. Y. Wang, M. D. Watson, J. Am. Chem. Soc. 2006, 128, 2536.
64. A. T. Prudchenko, S. A. Vereshchagina, V. A. Barkhash, N. N. Vorozhtsov, Zh. Obshch. Khim. 1967, 37, 2195.
65. T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 3072.
66. M. Kitahara, K. Hirano, H. Tsurugi, T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 1772
67. T. Kawano, N. Matsuyama, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2010, 75, 1764
68. T. Mukai, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 1360
69. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900
70. S. Guo, B. Qian, Y. Xie, C. Xia, H. Huang, Org. Lett. 2011, 13, 522
71. J. Wang, J.-T. Hou, J. Wen, J. Zhang, X.-Q. Yu, Chem. Commun. 2011, 47, 3652
72. M. Miyasaka, K. Hirano, T. Satoh, R. Kowalczyk, C. Bolm, M. Miura, Org. Lett. 2011, 13, 359
73. L.-H. Zou, Z.-B. Dong, C. Bolm, Synlett 2012, 1613
74. N. Matsuda, K. Hirano, T. Satoh, M. Miura, Synthesis 2012, 1792
75. L.-H. Zou, J. Reball, J. Mottweiler, C. Bolm, Chem. Commun. 2012, 48, 11307.
76. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833
77. Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem. Soc. 2009, 131, 7956.
78. During the preparation of our manuscript, the following two important papers appeared reporting a) the copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarenes (, S. Fan, Z. Chen, X. Zhang, Org. Lett. 2012, 14, 4950) and b) the dehydrogenative cross-coupling between two azoles
79. X. Qin, B. Feng, J. Dong, X. Li, Y. Xue, J. Lan, J. You, J. Org. Chem. 2012, 77, 7677).
80. I. Thomé, A. Nijs, C. Bolm, Chem. Soc. Rev. 2012, 41, 979
81. N. E. Leadbeater, Nat. Chem. 2010, 2, 1007.