Pd-catalyzed oxidative C-H/C-H cross-coupling of pyridines with heteroarenes

Chemical Science

Volumn 4, Issue 5, 2013, Pages 2163-2167

  Liu, Bo ^a   Huang, Yumin ^a   Lan, Jingbo ^a   Song, Feijie ^a   You, Jingsong ^a  

^a China   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-H ACTIVATION; CROSS-COUPLINGS; HETEROARENES; HETEROARYLATION;

ACTIVATION ANALYSIS;

PYRIDINE;

EID: 84875772487     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc50348h     Document Type: Article

References (58)

1. G. D. Henry, Tetrahedron, 2004, 60, 6043-6061
2. J. P. Michael, Nat. Prod. Rep. 2005, 22, 627-646
3. J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347
4. M. Schlosser, F. Mongin, Chem. Soc. Rev. 2007, 36, 1161-1172
5. C. G. Arena, G. Aricò, Curr. Org. Chem. 2010, 14, 546-580
6. D. Zhao, J. You, C. Hu, Chem.-Eur. J. 2011, 17, 5466-5492
7. D. R. Stuart, K. Fagnou, Science, 2007, 316, 1172-1175
8. D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072-12073
9. S.-L. You, J.-B. Xia, Top. Curr. Chem. 2010, 292, 165-194
10. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169
11. T. Newhouse, P. S. Baran, Angew. Chem. Int. Ed. 2011, 50, 3362-3374
12. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292
13. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885-1898
14. W. Han, A. R. Ofial, Synlett, 2011, 1951-1955
15. X. Bugaut, F. Glorius, Angew. Chem. Int. Ed. 2011, 50, 7479-7481
16. W. Han, P. Mayer, A. R. Ofial, Angew. Chem. Int. Ed. 2011, 50, 2178-2182
17. M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 6993-6997
18. S. Fan, Z. Chen, X. Zhang, Org. Lett. 2012, 14, 4950-4953
19. Z. Mao, Z. Wang, Z. Xu, F. Huang, Z. Yu, R. Wang, Org. Lett. 2012, 14, 3854-3857
20. X. Qin, B. Feng, J. Dong, X. Li, Y. Xue, J. Lan, J. You, J. Org. Chem. 2012, 77, 7677-7683
21. J. Dong, Y. Huang, X. Qin, Y. Cheng, J. Hao, D. Wan, W. Li, X. Liu, J. You, Chem.-Eur. J. 2012, 18, 6158-6162
22. N. Kuhl, M. N. Hopkinson, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 8230-8234
23. Y. Nakao, Synthesis, 2011, 3209-3219
24. Y. Wei, W. Su, J. Am. Chem. Soc. 2010, 132, 16377-16379
25. C.-Y. He, S. Fan, X. Zhang, J. Am. Chem. Soc. 2010, 132, 12850-12852
26. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, J. You, J. Am. Chem. Soc. 2010, 132, 1822-1824
27. Z. Wang, K. Li, D. Zhao, J. Lan, J. You, Angew. Chem. Int. Ed. 2011, 50, 5365-5369
28. X. Gong, G. Song, H. Zhang, X. Li, Org. Lett. 2011, 13, 1766-1769
29. A. D. Yamaguchi, D. Mandal, J. Yamaguchi, K. Itami, Chem. Lett. 2011, 40, 555-557
30. D. Mandal, A. D. Yamaguchi, J. Yamaguchi, K. Itami, J. Am. Chem. Soc. 2011, 133, 19660-19663
31. Z. Wang, F. Song, Y. Zhao, Y. Huang, L. Yang, D. Zhao, J. Lan, J. You, Chem.-Eur. J. 2012, 18, 16616-16620
32. X. Qin, H. Liu, D. Qin, Q. Wu, J. You, D. Zhao, Q. Guo, X. Huang, J. Lan, Chem. Sci. 2013, 10.1039/c3sc22241a
33. A. M. Berman, J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 14926-14927
34. M. Tobisu, I. Hyodo, N. Chatani, J. Am. Chem. Soc. 2009, 131, 12070-12071
35. A. M. Berman, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2010, 75, 7863-7868
36. M. Wasa, B. T. Worrell, J.-Q. Yu, Angew. Chem. Int. Ed. 2010, 49, 1275-1277
37. P. Guo, J. M. Joo, S. Rakshit, D. Sames, J. Am. Chem. Soc. 2011, 133, 16338-16341
38. I. B. Seiple, S. Su, R. A. Rodriguez, R. Gianatassio, Y. Fujiwara, A. L. Sobel, P. S. Baran, J. Am. Chem. Soc. 2010, 132, 13194-13196
39. S. Yanagisawa, K. Ueda, T. Tanaguchi, K. Itami, Org. Lett. 2008, 10, 4673-4676
40. F. Minisci, E. Vismara, F. Fontana, G. Morini, M. Serravalle, C. Giordano, J. Org. Chem. 1986, 51, 4411-4416
41. M. Ye, G.-L. Gao, A. J. F. Edmunds, P. A. Worthington, J. A. Morris, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19090-19093
42. J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 5332-5333
43. Y. Nakao, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 2448-2449
44. Y. Nakao, Y. Yamada, N. Kashihara, T. Hiyama, J. Am. Chem. Soc. 2010, 132, 13666-13668
45. M. Ye, G.-L. Gao, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 6964-6967
46. J. Kwak, Y. Ohk, Y. Jung, S. Chang, J. Am. Chem. Soc. 2012, 134, 17778-17788
47. D. G. Johnson, J. M. Lynam, N. S. Mistry, J. M. Slattery, R. J. Thatcher, A. C. Whitwood, J. Am. Chem. Soc. 2013, 135, 2222-2234
48. Q. Shen, T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 6586-6596
49. M. Su, S. L. Buchwald, Angew. Chem. Int. Ed. 2012, 51, 4710-4713
50. T. Kawashima, T. Takao, H. Suzuki, J. Am. Chem. Soc. 2007, 129, 11006-11007
51. K. Masui, H. Ikegami, A. Mori, J. Am. Chem. Soc. 2004, 126, 5074-5075
52. M. Takahashi, K. Masui, H. Sekiguchi, N. Kobayashi, A. Mori, M. Funahashi, N. Tamaoki, J. Am. Chem. Soc. 2006, 128, 10930-10933
53. J.-B. Xia, X.-Q. Wang, S.-L. You, J. Org. Chem. 2009, 74, 456-458
54. Y. Li, J. Jin, W. Qian, W. Bao, Org. Biomol. Chem. 2010, 8, 326-330
55. M. Zhu, K. Fujita, R. Yamaguchi, Chem. Commun. 2011, 47, 12876-12878
56. K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047-14049
57. N. Kuhl, M. N. Hopkinson, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 8230-8234
58. J. Dong, Y. Huang, X. Qin, Y. Cheng, J. Hao, D. Wan, W. Li, X. Liu, J. You, Chem.-Eur. J. 2012, 18, 6158-6162