Copper-mediated hydroxylation of arenes and heteroarenes directed by a removable bidentate auxiliary

Organic Letters

Volumn 16, Issue 15, 2014, Pages 3904-3907

  Li, Xin ^a   Liu, Yan Hua ^a   Gu, Wen Jia ^a   Li, Bo ^a   Chen, Fa Jie ^a   Shi, Bing Feng ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE; 1,4-DIHYDROPYRIDINE; BENZAMIDE DERIVATIVE; BENZENE DERIVATIVE; COPPER; DIHYDROPYRIDINE DERIVATIVE; LIGAND; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; SYNTHESIS;

BENZAMIDES; BENZENE DERIVATIVES; CATALYSIS; COPPER; DIHYDROPYRIDINES; HYDROXYLATION; LIGANDS; MOLECULAR STRUCTURE; PHENOLS;

EID: 84905409253     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5016064     Document Type: Article

References (55)

1. Huang, W.-Y.; Cai, Y.-Z.; Zhang, Y. Nutr. Cancer 2010, 62, 1
2. Rappoport, Z. The Chemistry of Phenols; John Wiley & Sons Ltd: Chichester, 2003.
3. Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: New York, 1996.
4. For selected recent reviews on oxygenation of C-H bond, see
5. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
6. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
7. Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912
8. Jintoku, T.; Nishimura, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1990, 1687
9. Zhang, Y. H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654
10. Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.-F.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827
11. Zhang, H.-Y.; Yi, H.-M.; Wang, G.-W.; Yang, B.; Yang, S.-D. Org. Lett. 2013, 15, 6186
12. Choy, P. Y.; Kwong, F. Y. Org. Lett. 2013, 15, 270
13. Thirunavukkarasu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett. 2012, 14, 4210
14. Mo, F.; Trzepkowski, L. J.; Dong, G. Angew. Chem., Int. Ed. 2012, 51, 13075
15. Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew. Chem., Int. Ed. 2012, 51, 13070 and references therein
16. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
17. Liu, Q.; Wu, P.; Yang, Y.; Zeng, Z.; Liu, J.; Yi, H.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 4666
18. Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464
19. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
20. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
21. Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842
22. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
23. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
24. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
25. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898
26. Ting, C. P.; Maimone, T. J. Angew. Chem., Int. Ed. 2014, 53, 3115
27. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030
28. Ma, Y.-Y.; Li, W.; Yu, B. Acta Chim. Sin. 2013, 71, 541
29. Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 8070
30. Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076
31. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
32. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237
33. Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342
34. Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 4457
35. Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797
36. Wang, Z.; Ni, J.-Z.; Kuninobu, Y.; Kanai, M. Angew. Chem., Int. Ed. 2014, 53, 3496
37. Wu, X.; Zhao, Y.; Zhang, G.; Ge, H. Angew. Chem., Int. Ed. 2014, 53, 3706
38. Li, Q.; Zhang, S.-Y.; He, G.; Ai, Z.; Nack, W. A.; Chen, G. Org. Lett. 2014, 16, 1764
39. Shang, M.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 3354
40. Dong, J.; Wang, F.; You, J. Org. Lett. 2014, 16, 2884 and references therein
41. Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932
42. Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411
43. Zhao, H.; Wang, M.; Su, W.; Hong, M. Adv. Synth. Catal. 2010, 352, 1301
44. Wei, Y.; Zhao, H.; Kan, J.; Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522
45. Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217
46. Kitahara, M.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2011, 133, 2160
47. Gallardo-Donaire, J.; Martin, R. J. Am. Chem. Soc. 2013, 135, 9350
48. Bhadra, S.; Matheis, C.; Katayev, D.; Gooβen, L. J. Angew. Chem., Int. Ed. 2013, 52, 9279 and references therein
49. Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187
50. Zhang, Q.; Chen, K.; Rao, W.-H.; Zhang, Y.-J.; Chen, F.-J.; Shi, B.-F. Angew. Chem., Int. Ed. 2013, 52, 13588
51. Hufman, L. M.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 9196
52. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
53. Wang, Z.-L.; Zhao, L.; Wang, M.-X. Org. Lett. 2011, 13, 6560
54. Zhou, J.; Li, B.; Hu, F.; Shi, B.-F. Org. Lett. 2013, 15, 3460
55. Zhou, J.; Li, B.; Qian, Z.-C.; Shi, B.-F. Adv. Synth. Catal. 2014, 356, 1038