Copper-mediated direct aryloxylation of benzamides assisted by an N, O -bidentate directing group

Organic Letters

Volumn 16, Issue 4, 2014, Pages 1104-1107

  Hao, Xin Qi ^a   Chen, Li Juan ^a   Ren, Baozeng ^b   Li, Liu Yan ^a   Yang, Xin Yan ^a   Gong, Jun Fang ^a   Niu, Jun Long ^a   Song, Mao Ping ^a  

^a Key Laboratory of Chemical Biology and Organic Chemistry of Henan   (China)

^b ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894547447     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500166d     Document Type: Article

References (63)

1. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
2. Takeuchi, D.; Asano, I.; Osakada, K. J. Org. Chem. 2006, 71, 8614
3. Wang, C.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 4194
4. Maetani, S.; Fukuyama, T.; Ryu, I. Org. Lett. 2013, 15, 2754
5. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581
6. Zhang, H.; Shi, R.; Gan, P.; Liu, C.; Ding, A.; Wang, Q.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5204
7. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
8. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 2337
9. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
10. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
11. Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853
12. Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539
13. Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 46, 8005
14. Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224
15. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369
16. Bistri, O.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 586
17. Kim, H. J.; Kim, M.; Chang, S. Org. Lett. 2011, 13, 2368
18. Zheng, X.; Ding, J.; Chen, J.; Gao, W.; Liu, M.; Wu, H. Org. Lett. 2011, 13, 1726
19. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
20. Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912
21. Liu, W.; Ackermann, L. Org. Lett. 2013, 15, 3484
22. Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.-F.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827
23. Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew. Chem., Int. Ed. 2012, 51, 13070
24. Gulevich, A. V.; Melkonyan, F. S.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 5528
25. Bhadra, S.; Matheis, C.; Katayev, D.; Gooβen, L. J. Angew. Chem., Int. Ed. 2013, 52, 1
26. Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285
27. Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476
28. Kuram, M. R.; Bhanuchandra, M.; Sahoo, A. K. Angew. Chem., Int. Ed. 2013, 52, 4607
29. Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250
30. Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504
31. Zhao, J.; Wang, Y.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2012, 14, 1078
32. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
33. While this manuscript was in preparation, Daugulis and co-workers reported the copper-catalyzed etherification of meta-or/and para -substituted arenes with picolinamide or 8-aminoquinoline directing groups: Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842
34. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
35. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450
36. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
37. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
38. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
39. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
40. Kozhushkov, S. I.; Ackermann, L. Chem. Sci. 2013, 4, 886
41. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
42. For a recent review on direct C-H functionalization through the aid of a bidentate directing group, see: Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
43. Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391
44. Giri, R.; Maugel, N.; Foxman, B. M.; Yu, J.-Q. Organometallics 2008, 27, 1667
45. Gou, F.-R.; Wang, X.-C.; Huo, P.-F.; Bi, H.-P.; Guan, Z.-H.; Liang, Y.-M. Org. Lett. 2009, 11, 5726
46. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
47. Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414
48. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030
49. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308
50. Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 14952
51. Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898
52. Aihara, Y.; Chatani, N. Chem. Sci. 2013, 4, 664
53. Rouqueta, G.; Chatani, N. Chem. Sci. 2013, 4, 2201
54. Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342
55. Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043
56. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237
57. Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 4457
58. Niu, J.-L.; Hao, X.-Q.; Gong, J.-F.; Song, M.-P. Dalton Trans. 2011, 40, 5135
59. Hao, X.-Q.; Xu, Y.-X.; Yang, M.-J.; Wang, L.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. Organometallics 2012, 31, 835
60. Wang, T.; Hao, X.-Q.; Huang, J.-J.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. J. Org. Chem. 2013, 78, 8712
61. Wang, T.; Niu, J.-L.; Liu, S.-L.; Huang, J.-J.; Gong, J.-F.; Song, M.-P. Adv. Synth. Catal. 2013, 355, 927
62. Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986
63. Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797