Copper-mediated direct alkoxylation of arenes using an N, O -bidentate directing system

Journal of Organic Chemistry

Volumn 79, Issue 21, 2014, Pages 10399-10409

  Zhang, Lin Bao ^a   Hao, Xin Qi ^a   Zhang, Shou Kun ^a   Liu, Ke ^a   Ren, Baozeng ^a   Gong, Jun Fang ^a   Niu, Jun Long ^a   Song, Mao Ping ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; FUNCTIONAL GROUPS;

2-AMINOPYRIDINE; ALKOXYLATION; DIRECTING GROUPS; HETEROARENES; HEXAFLUOROISOPROPANOL; REACTION SYSTEM;

AROMATIC COMPOUNDS;

2 AMINOPYRIDINE DERIVATIVE; 8 AMINOQUINOLINE DERIVATIVE; ALCOHOL DERIVATIVE; BENZOIC ACID DERIVATIVE; COPPER; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; 2-AMINOPYRIDINE 1-OXIDE; AMINE OXIDE; AMINOPYRIDINE DERIVATIVE; BENZOIC ACID;

ALKOXYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHLORINATION; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; COVALENT BOND; DNA BASE COMPOSITION; ELECTRON; ELECTRON TRANSPORT; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

AMINOPYRIDINES; BENZOIC ACID; CATALYSIS; COPPER; CYCLIC N-OXIDES; MOLECULAR STRUCTURE;

EID: 84909992207     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502005j     Document Type: Article

References (109)

1. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
2. Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
3. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
4. Lewis, L. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013
5. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
6. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
7. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
8. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082
9. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
10. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
11. Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170
12. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
13. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
14. Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588
15. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
16. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
17. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
18. John, A.; Nicholas, K. M. J. Org. Chem. 2011, 76, 4158
19. Pan, J.; Su, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 8647
20. Wang, H.; Yu, Y.; Hong, X.; Tan, Q.; Xu, B. J. Org. Chem. 2014, 79, 3279
21. Xu, H.; Qiao, X.; Yang, S.; Shen, Z. J. Org. Chem. 2014, 79, 4414
22. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
23. 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
24. Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504
25. Zhao, J.; Wang, Y.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2012, 14, 1078
26. Zhang, C.; Feng, P.; Jiao, N. J. Am. Chem. Soc. 2013, 135, 15257
27. Takemura, N.; Kuninobu, Y.; Kanai, M. Org. Lett. 2013, 15, 844
28. Shan, G.; Yang, X.; Zong, Y.; Rao, Y. Angew. Chem., Int. Ed. 2013, 52, 13606
29. Musaev, D. G.; Figg, T. M.; Kaledin, A. L. Chem. Soc. Rev. 2014, 43, 5009
30. Wu, Y.; Wang, J.; Mao, F.; Kwong, F. Y. Chem.-Asian J. 2014, 9, 26
31. Franzoni, I.; Mazet, C. Org. Biomol. Chem. 2014, 12, 233
32. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
33. Jayakumar, J.; Parthasarathy, K.; Chen, Y.-H.; Lee, T.-H.; Chuang, S.-C.; Cheng, C.-H. Angew. Chem., Int. Ed. 2014, 53, 9889 and references therein
34. Ackermann, L. Chem. Rev. 2011, 111, 1315
35. Ackermann, L. Acc. Chem. Res. 2014, 47, 281
36. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
37. Kitahara, M.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2011, 133, 2160
38. Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 4457
39. Odani, R.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013, 78, 11045
40. Mao, Z.; Wang, Z.; Xu, Z.; Huang, F.; Yu, Z.; Wang, R. Org. Lett. 2012, 14, 3854
41. Fan, S.; Chen, Z.; Zhang, X. Org. Lett. 2012, 14, 4950
42. Qin, X.; Feng, B.; Dong, J.; Li, X.; Xue, Y.; Lan, J.; You, J. J. Org. Chem. 2012, 77, 7677
43. Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912
44. Altman, R. A.; Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Org. Chem. 2008, 73, 284
45. Hartwig, J. F. Nature 2008, 455, 314
46. For a review of Ullmann-type coupling reactions, see: Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
47. For a review, see: Qiao, J. X.; Lam, P. Y. S. Synthesis 2011, 829
48. For a book, see: Li, J. J. Name Reactions; Springer: New York, 2014; p 628.
49. For a review, see: Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Balaraman, E.; Pavan Kumar, K. V. P. Chem. Rev. 2009, 109, 2551
50. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; Jørgensen, K. A.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 784
51. Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.-F.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827
52. Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654
53. Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew. Chem., Int. Ed. 2012, 51, 13070
54. Mo, F.; Trzepkowski, L. J.; Dong, G. Angew. Chem., Int. Ed. 2012, 51, 13075
55. Emmert, M. H.; Cook, A. K.; Xie, Y. J.; Sanford, M. S. Angew. Chem., Int. Ed. 2011, 50, 9409
56. Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236
57. Wang, W.; Luo, F.; Zhang, S.; Cheng, J. J. Org. Chem. 2010, 75, 2415
58. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357
59. Kumpulainen, E. T. T.; Koskinen, A. M. P. Chem.-Eur. J. 2009, 15, 10901
60. Okada, T.; Awasa, T.; Sugiyama, Y.; Kirihara, M.; Iwai, T.; Kimura, Y. Synlett 2014, 25, 596
61. Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203
62. Jiang, T.-S.; Wang, G.-W. J. Org. Chem. 2012, 77, 9504
63. Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300
64. Li, W.; Sun, P. J. Org. Chem. 2012, 77, 8362
65. Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141
66. Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476
67. Wang, H.; Li, G.; Engle, K. M.; Yu, J.-Q.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6774
68. Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105
69. Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187
70. Gao, T.; Sun, P. J. Org. Chem. 2014, 79, 9888
71. Bhadra, S.; Dzik, W. I.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 2959
72. Bhadra, S.; Matheis, C.; Katayev, D.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 9279
73. Huffman, L. M.; Casitas, A.; Font, M.; Canta, M.; Costas, M.; Ribas, X.; Stahl, S. S. Chem.-Eur. J. 2011, 17, 10643
74. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
75. Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797
76. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
77. Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342
78. Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043
79. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237
80. Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842
81. Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53, 10209
82. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030
83. Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898
84. Aihara, Y.; Chatani, N. Chem. Sci. 2013, 4, 664
85. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308
86. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
87. Zhang, S.-Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313
88. Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124
89. Li, Q.; Zhang, S.-Y.; He, G.; Ai, Z.; Nack, W. A.; Chen, G. Org. Lett. 2014, 16, 1764
90. Li, X.; Liu, Y.-H.; Gu, W.-J.; Li, B.; Chen, F.-J.; Shi, B.-F. Org. Lett. 2014, 16, 3904
91. Dong, J.; Wang, F.; You, J. Org. Lett. 2014, 16, 2884
92. Wu, X.; Zhao, Y.; Zhang, G.; Ge, H. Angew. Chem., Int. Ed. 2014, 53, 3706
93. Sun, W.-W.; Cao, P.; Mei, R.-Q.; Li, Y.; Ma, Y.-L.; Wu, B. Org. Lett. 2014, 16, 480
94. Zhang, L.-S.; Chen, G.; Wang, X.; Guo, Q.-Y.; Zhang, X.-S.; Pan, F.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2014, 53, 3899
95. Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2012, 14, 3724
96. Rodríguez, N.; Romero-Revilla, J. A.; Fernández-Ibáñez, M. á.; Carretero, J. C. Chem. Sci. 2013, 4, 175
97. Ye, X.; He, Z.; Ahmed, T.; Weise, K.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Chem. Sci. 2013, 4, 3712
98. Gu, Q.; Al Mamari, H. H.; Graczyk, K.; Diers, E.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 3868
99. Huang, L.; Sun, X.; Li, Q.; Qi, C. J. Org. Chem. 2014, 79, 6720
100. For a recent review of direct C-H functionalization aided by a bidentate directing group, see: Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
101. Hao, X.-Q.; Chen, L.-J.; Ren, B.; Li, L.-Y.; Yang, X.-Y.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. Org. Lett. 2014, 16, 1104
102. Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901
103. Gamez, P.; Reedijk, I. W. C. E. J.; Sheldon, R. A. Chem. Commun. 2003, 2414
104. Sun, R.; Liu, Y.; Zhang, Y.; Xiong, Li.; Wang, Q. J. Agric. Food Chem. 2011, 59, 2471
105. Xu, X. Y.; Qian, X. H.; Li, Z.; Huang, Q. C. J. Fluorine Chem. 2003, 121, 51
106. Mirica, L. M.; Ottenwaelder, X.; Stack, D. P. Chem. Rev. 2004, 104, 1013
107. Chen, P.; Root, D. E.; Campochiaro, C.; Fujisawa, K.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 466
108. Klinman, J. P. Chem. Rev. 1996, 96, 2541
109. Whittaker, J. W. Chem. Rev. 2003, 103, 2347