Copper-catalyzed site-selective intramolecular amidation of unactivated C(sp3)-H bonds

Angewandte Chemie - International Edition

Volumn 53, Issue 14, 2014, Pages 3706-3710

  Wu, Xuesong ^a   Zhao, Yan ^a   Zhang, Guangwu ^a,b   Ge, Haibo ^a  

^a INDIANA UNIVERSITY   (United States)

^b NANJING UNIVERSITY   (China)

Author keywords

C H activation; copper; heterocycles; homogeneous catalysis; synthetic methods

Indexed keywords

ACTIVATION ANALYSIS; AMIDES; AROMATIC COMPOUNDS; CARBON; CATALYSIS; FUNCTIONAL GROUPS; LIGANDS; REACTION KINETICS;

ALIPHATIC AMIDES; BIDENTATE LIGANDS; C-H ACTIVATION; C-H BOND FUNCTIONALIZATION; FIVE-MEMBERED RINGS; HETEROCYCLES; HOMOGENEOUS CATALYSIS; SYNTHETIC METHODS;

COPPER;

EID: 84897408695     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201311263     Document Type: Article

References (109)

1. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
2. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
3. Angew. Chem. Int. Ed. 2009, 48, 5094
4. M. Wasa, K. M. Engle, J.-Q. Yu, Isr. J. Chem. 2010, 50, 605
5. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
6. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654
7. L. Ackermann, Chem. Commun. 2010, 46, 4866
8. H. Li, B.-J. Li, Z.-J. Shi, Catal. Sci. Technol. 2011, 1, 191
9. N. Yoshikai, Synlett 2011, 1047
10. H. M. L. Davies, J. Du Bois, J.-Q. Yu, Chem. Soc. Rev. 2011, 40, 1855
11. W. R. Gutekunst, P. S. Baran, Chem. Soc. Rev. 2011, 40, 1976
12. J. F. Hartwig, Chem. Soc. Rev. 2011, 40, 1992
13. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422
14. Angew. Chem. Int. Ed. 2011, 50, 3362
15. O. Baudoin, Chem. Soc. Rev. 2011, 40, 4902
16. M. C. White, Science 2012, 335, 807
17. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814.
18. G. Rouquet, N. Chatani, Angew. Chem. 2013, 125, 11942
19. Angew. Chem. Int. Ed. 2013, 52, 11726.
20. B. D. Dangel, K. Godula, S. W. Youn, B. Sezen, D. Sames, J. Am. Chem. Soc. 2002, 124, 11856.
21. V. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154
22. B. V. S. Reddy, L. R. Reddy, E. J. Corey, Org. Lett. 2006, 8, 3391
23. R. Giri, N. Maugel, B. M. Foxman, J.-Q. Yu, Organometallics 2008, 27, 1667
24. D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965
25. G. He, G. Chen, Angew. Chem. 2011, 123, 5298
26. Angew. Chem. Int. Ed. 2011, 50, 5192
27. Y. Ano, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2011, 133, 12984
28. G. He, Y.-S. Zhao, S.-Y. Zhang, C.-X. Lu, G. Chen, J. Am. Chem. Soc. 2012, 134, 3
29. E. T. Nadres, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 7
30. Y. Ano, M. Tobisu, N. Chatani, Org. Lett. 2012, 14, 354
31. R. K. Rit, M. R. Yadav, A. K. Sahoo, Org. Lett. 2012, 14, 3724
32. L. D. Tran, O. Daugulis, Angew. Chem. 2012, 124, 5278
33. Angew. Chem. Int. Ed. 2012, 51, 5188
34. N. Rodríguez, J. A. Romero-Revilla, M. Á. Fernández-Ibáñez, J. C. Carretero, Chem. Sci. 2013, 4, 175
35. S.-Y. Zhang, G. He, W. A. Nack, Y. Zhao, Q. Li, G. Chen, J. Am. Chem. Soc. 2013, 135, 2124
36. K. Chen, F. Hu, S.-Q. Zhang, B.-F. Shi, Chem. Sci. 2013, 4, 3906
37. G. He, S.-Y. Zhang, W. A. Nack, Q. Li, G. Chen, Angew. Chem. 2013, 125, 11330
38. Angew. Chem. Int. Ed. 2013, 52, 11124
39. Q. Zhang, K. Chen, W.-H. Rao, Y.-J. Zhang, F.-J. Chen, B.-F. Shi, Angew. Chem. 2013, 125, 13833
40. Angew. Chem. Int. Ed. 2013, 52, 13588
41. W.-W. Sun, P. Cao, R.-Q. Mei, Y. Li, Y.-L. Ma, B. Wu, Org. Lett. 2014, 16, 480.
42. N. Hasegawa, V. Charra, S. Inoue, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 8070
43. N. Hasegawa, K. Shibata, V. Charra, S. Inoue, Y. Fukumoto, N. Chatani, Tetrahedron 2013, 69, 4466.
44. R. Shang, L. Ilies, A. Matsumoto, E. Nakamura, J. Am. Chem. Soc. 2013, 135, 6030.
45. X.-S. Wu, Y. Zhao, H.-B. Ge, J. Am. Chem. Soc. 2014, 136, 1789.
46. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790
47. M. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14058
48. L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 18237
49. T. Truong, K. Klimovica, O. Daugulis, J. Am. Chem. Soc. 2013, 135, 9342
50. J. Roane, O. Daugulis, Org. Lett. 2013, 15, 5842
51. L. D. Tran, J. Roane, O. Daugulis, Angew. Chem. 2013, 125, 6159
52. Angew. Chem. Int. Ed. 2013, 52, 6043.
53. G. S. Singh, M. D-hooghe, N. De Kimpe, Tetrahedron 2011, 67, 1989
54. A. MacGowan, Curr. Opin. Pharmacol. 2011, 11, 470
55. P. Galletti, D. Giacomini, Curr. Med. Chem. 2011, 18, 4265
56. A. Kamath, I. Ojima, Tetrahedron 2012, 68, 10640
57. S. G. Kurz, R. A. Bonomo, Expert Rev. Anti-Infect. Ther. 2012, 10, 999
58. I. Balderas-Renteria, P. Gonzalez-Barranco, A. Garcia, B. K. Banik, G. Rivera, Curr. Med. Chem. 2012, 19, 4377
59. T. Orbegozo, F. Burel, P. Jubault, X. Pannecoucke, Tetrahedron 2013, 69, 4015
60. K. Tahlan, S. E. Jensen, J. Antibiot. 2013, 66, 401
61. D. A. Leonard, R. A. Bonomo, R. A. Powers, Acc. Chem. Res. 2013, 46, 2407
62. J. Chen, X.-H. Shang, F. Hu, X.-Z. Lao, X.-D. Gao, H. Zheng, W.-B. Yao, Mini-Rev. Med. Chem. 2013, 13, 1846.
63. C.-J. Li, Acc. Chem. Res. 2009, 42, 335
64. W.-J. Yoo, C.-J. Li, Top. Curr. Chem. 2010, 292, 281
65. C. J. Scheuermann, Chem. Asian J. 2010, 5, 436
66. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
67. C. Liu, H. Zhang, W. Shi, A.-W. Lei, Chem. Rev. 2011, 111, 1780
68. M. Schnürch, N. Dastbaravardeh, M. Ghobrial, B. Mrozek, M. D. Mihovilovic, Curr. Org. Chem. 2011, 15, 2694
69. A. W. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem. 2011, 123, 11256
70. Angew. Chem. Int. Ed. 2011, 50, 11062
71. C. Zhang, C.-H. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3464. For selected recent examples, see
72. P. S. Baran, M. P. DeMartino, Angew. Chem. 2006, 118, 7241
73. Angew. Chem. Int. Ed. 2006, 45, 7083
74. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833
75. G. Brasche, S. L. Buchwald, Angew. Chem. 2008, 120, 1958
76. Angew. Chem. Int. Ed. 2008, 47, 1932
77. S. Ueda, H. Nagasawa, Angew. Chem. 2008, 120, 6511
78. Angew. Chem. Int. Ed. 2008, 47, 6411
79. O. Baslé, C.-J. Li, Chem. Commun. 2009, 4124
80. S. Ueda, H. Nagasawa, J. Am. Chem. Soc. 2009, 131, 15080
81. S. Ueda, H. Nagasawa, J. Org. Chem. 2009, 74, 4272
82. C. Zhang, N. Jiao, J. Am. Chem. Soc. 2010, 132, 28
83. C. Zhang, N. Jiao, Angew. Chem. 2010, 122, 6310
84. Angew. Chem. Int. Ed. 2010, 49, 6174
85. H. Wang, Y. Wang, C. Peng, J. Zhang, Q. Zhu, J. Am. Chem. Soc. 2010, 132, 13217
86. H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang, Q. Zhu, Angew. Chem. 2011, 123, 5796
87. Angew. Chem. Int. Ed. 2011, 50, 5678
88. L. M. Huffman, A. Casitas, M. Font, M. Canta, M. Costas, X. Ribas, S. S. Stahl, Chem. Eur. J. 2011, 17, 10643
89. L. Zhang, Z.-H. Liu, H.-Q. Li, G.-C. Fang, B.-D. Barry, T. A. Belay, X.-H. Bi, Q. Liu, Org. Lett. 2011, 13, 6536
90. K. K. Toh, Y.-F. Wang, E. P. J. Ng, S. Chiba, J. Am. Chem. Soc. 2011, 133, 13942
91. Y.-F. Wang, X. Zhu, S. Chiba, J. Am. Chem. Soc. 2012, 134, 3679
92. Z.-J. Xu, C. Zhang, N. Jiao, Angew. Chem. 2012, 124, 11529
93. Angew. Chem. Int. Ed. 2012, 51, 11367.
94. Y.-F. Wang, H. Chen, X. Zhu, S. Chiba, J. Am. Chem. Soc. 2012, 134, 11980
95. H. Chen, S. Sanjaya, Y.-F. Wang, S. Chiba, Org. Lett. 2013, 15, 212.
96. E. M. Simmons, J. F. Hartwig, Angew. Chem. 2012, 124, 3120
97. Angew. Chem. Int. Ed. 2012, 51, 3066.
98. H. Furuta, H. Maeda, A. Osuka, J. Am. Chem. Soc. 2000, 122, 803
99. X. Ribas, D. A. Jackson, B. Donnadieu, J. Mahía, T. Parella, R. Xifra, B. Hedman, K. O. Hodgson, A. Llobet, T. D. P. Stack, Angew. Chem. 2002, 114, 3117
100. Angew. Chem. Int. Ed. 2002, 41, 2991
101. H. Maeda, A. Osuka, H. Furuta, J. Am. Chem. Soc. 2003, 125, 15690
102. R. Xifra, X. Ribas, A. Llobet, A. Poater, M. Duran, M. Solà, T. D. P. Stack, J. Benet-Buchholz, B. Donnadieu, J. Mahía, T. Parella, Chem. Eur. J. 2005, 11, 5146
103. M. Pawlicki, I. Kanska, L. Latos-Graźynski, Inorg. Chem. 2007, 46, 6575
104. L. M. Huffman, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 9196
105. B. Yao, D.-X. Wang, Z.-T. Huang, M.-X. Wang, Chem. Commun. 2009, 2899
106. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 1147
107. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068
108. X. Ribas, C. Calle, A. Poater, A. Casitas, L. Gõmez, R. Xifra, T. Parella, J. Benet-Buchholz, A. Schweiger, G. Mitrikas, M. Solà, A. Llobet, T. D. P. Stack, J. Am. Chem. Soc. 2010, 132, 12299
109. A. M. Suess, M. Z. Ertem, C. J. Cramer, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 9797.