Copper-catalyzed oxidative arylation of heteroarenes under mild conditions using dioxygen as the sole oxidant

Chemistry - A European Journal

Volumn 17, Issue 23, 2011, Pages 6321-6325

  Yang, Fanzhi ^a,b   Xu, Zhaoqing ^a   Wang, Zhe ^a,b   Yu, Zhengkun ^a   Wang, Rui ^b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

arylation; boronic ester; copper; cross coupling; heterocycles

Indexed keywords

CATALYSIS; COPPER; ESTERS; OXIDANTS;

ARYLATIONS; BORONIC ESTERS; COPPER CATALYZED; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; HETEROARENES; HETEROCYCLES; OXIDATIVE ARYLATION;

AROMATIC COMPOUNDS;

EID: 79958237657     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100136     Document Type: Article

References (66)

1. F. Diederich, P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1988
2. L. Ackermann, Modern Arylation Methods, Wiley-VCH, Weinheim, 2009.
3. Some selected examples
4. J. C. Lewis, A. M. Berman, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 2493-2500
5. S. Yanagisawa, T. Sudo, R. Noyori, K. Itami, J. Am. Chem. Soc. 2006, 128, 11748-11749
6. X. Wang, B. S. Lane, D. Sames, J. Am. Chem. Soc. 2005, 127, 4996-4997
7. N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972-4973
8. G. L. Turner, J. A. Morris, M. F. Greaney, Angew. Chem. 2007, 119, 8142-8146
9. Angew. Chem. Int. Ed. 2007, 46, 7996-8000
10. C. Bressy, D. Alberico, M. Lautens, J. Am. Chem. Soc. 2005, 127, 13148-13149
11. T. Okazawa, M. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 5286-5287
12. T. Martin, C. Verrier, C. Hoarau, F. Marsais, Org. Lett. 2008, 10, 2909-2912
13. M. Nakano, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1851-1854
14. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172-1175
15. L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. 2009, 121, 9976-10011
16. Angew. Chem. Int. Ed. 2009, 48, 9792-9826
17. J. Huang, J. Chan, Y. Chan, C. J. Borths, K. D. Baucom, R. D. Larsen, M. M. Faul, J. Am. Chem. Soc. 2010, 132, 3674-3675
18. K. Xie, Z. Yang, X. Zhou, X. Li, S. Wang, Z. Tan, X. An, C.-C. Guo, Org. Lett. 2010, 12, 1564-1567.
19. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404-12405
20. D. Zhao, W. Wang, F. Yang, J. Lan, L. Yang, G. Gao, J. You, Angew. Chem. 2009, 121, 3346-3350
21. Angew. Chem. Int. Ed. 2009, 48, 3296-3300
22. J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett. 2009, 11, 1733-1736
23. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 1737-1740.
24. Some selected examples
25. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639
26. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238
27. M. Lersch, M. Tilset, Chem. Rev. 2005, 105, 2471-2526
28. J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507-514
29. K. Godula, D. Sames, Science 2006, 312, 67-72
30. B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276-9282
31. Y. Zhao, H. Wang, X. Hou, Y. Hu, A. Lei, H. Zhang, L. Zhu, J. Am. Chem. Soc. 2006, 128, 15048-15049
32. P. Baran, M. P. DeMartino, Angew. Chem. 2006, 118, 7241-7244
33. Angew. Chem. Int. Ed. 2006, 45, 7083-7086
34. S. R. Dubbaka, M. Kienle, H. Mayr, P. Knochel, Angew. Chem. 2007, 119, 9251-9255
35. Angew. Chem. Int. Ed. 2007, 46, 9093-9096
36. G. Cahiez, L. Foulgoc, A. Moyeux, Angew. Chem. 2009, 121, 3013-3016
37. Angew. Chem. Int. Ed. 2009, 48, 2969-2972
38. G. Cahiez, C. Duplais, J. Buendia, Angew. Chem. 2009, 121, 6859-6862
39. Angew. Chem. Int. Ed. 2009, 48, 6731-6734
40. M. Chen, X. Zheng, W. Li, J. He, A. Lei, J. Am. Chem. Soc. 2010, 132, 4101-4103.
41. J. Piera, J.-E. Backväll, Angew. Chem. 2008, 120, 3558-3576
42. Angew. Chem. Int. Ed. 2008, 47, 3506-3523
43. S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501
44. Angew. Chem. Int. Ed. 2004, 43, 3400-3420
45. M. S. Sigman, M. J. Schultz, Org. Biomol. Chem. 2004, 2, 2551-2554.
46. H. Zhao, M. Wang, W. Su, M. Hong, Adv. Synth. Catal. 2010, 352, 1301-1306
47. for Ag-mediated amination of benzoxazoles, see:, S. H. Cho, J. Y. Kim, S. Y. Lee, S. Chang, Angew. Chem. 2009, 121, 9291-9294
48. Angew. Chem. Int. Ed. 2009, 48, 9127-9130.
49. For nickel-catalyzed oxidative alkynylation of azoles, see:, N. Matsuyama, M. Kitahara, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2358-2361
50. for copper-mediated C-H bond arylation of arenes with arylboronic acids, see:, I. Ban, T. Sudo, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 3607-3609
51. for copper-catalyzed oxidative cross-coupling between polyfluoroarenes and terminal alkynes, see:, Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522-2523.
52. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2010, 122, 2248-2251
53. Angew. Chem. Int. Ed. 2010, 49, 2202-2205.
54. B. Liu, X. Qin, K. Li, X. Li, X. Guo, J. Lan, J. You, Chem. Eur. J. 2010, 16, 11836-11839.
55. S. Ranjit, X. Liu, Chem. Eur. J. 2011, 17, 1105-1108.
56. H. Hachiya, K. Hirano, T. Satoh, M. Miura, ChemCatChem 2010, 2, 1403-1406.
57. An attempt of arylating azole and thiazole by using a reported method failed., S.-D. Yang, C.-L. Sun, Z. Fang, B.-J. Li, Y.-Z. Li, Z.-J. Shi, Angew. Chem. 2008, 120, 1495-1498
58. Angew. Chem. Int. Ed. 2008, 47, 1473-1476.
59. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2009, 131, 17052-17053.
60. C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415-3434.
61. C. Glaser, Chem. Ber. 1869, 2, 422-424.
62. A. E. King, T. C. Brunold, S. S. Stahl, J. Am. Chem. Soc. 2009, 131, 5044-5045
63. X. Ribas, C. Calle, A. Poater, A. Casitas, L. Gmez, R. Xifra, T. Parella, J. Benet-Buchholz, A. Schweiger, G. Mitrikas, M. Sol, A. Llobet, T. D. P. Stack, J. Am. Chem. Soc. 2010, 132, 12299-12306
64. A. Casitas, A. E. King, T. Parella, M. Coatas, S. S. Stahl, X. Ribas, Chem. Sci. 2010, 1, 326-330.
65. 2)]-catalyzed homocoupling of arylboronic acid has been reported by Jutand and co-workers
66. C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836.