Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles

Angewandte Chemie - International Edition

Volumn 52, Issue 16, 2013, Pages 4457-4461

  Nishino, Mayuko ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C H cleavage; copper; cross coupling; heterobiaryls; synthetic methods

Indexed keywords

BENZOIC ACID DERIVATIVES; C-H BOND CLEAVAGE; C-H CLEAVAGE; COUPLING REACTION; CROSS-COUPLINGS; HETEROBIARYLS; RATE-LIMITING STEPS; SYNTHETIC METHODS;

BENZOIC ACID; CHEMICAL REACTIONS;

COPPER;

BENZOIC ACID; COPPER; ORGANOMETALLIC COMPOUND; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AZOLES; BENZOIC ACID; COPPER; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84876273684     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300587     Document Type: Article

References (91)

1. C. Liu, H. Zhang, W. Sui, A. Lei, Chem. Rev. 2011, 111, 1780
2. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092
3. Angew. Chem. Int. Ed. 2012, 51, 8960; see the Supporting Information for complete citations.
4. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529.
5. J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2000, 122, 6321.
6. V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154
7. D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965
8. E. T. Nadres, O. Daudulis, J. Am. Chem. Soc. 2012, 134, 7
9. L. D. Tran, O. Daugulis, Angew. Chem. 2012, 124, 5278
10. Angew. Chem. Int. Ed. 2012, 51, 5188.
11. R. Giri, N. Maugel, B. M. Foxman, J.-Q. Yu, Organometallics 2008, 27, 1667.
12. S. Inoue, H. Shiota, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2009, 131, 6898
13. N. Hasegawa, V. Charra, S. Inoue, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 8070
14. Y. Ano, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2011, 133, 12984
15. Y. Ano, M. Tobisu, N. Chatani, Org. Lett. 2012, 14, 354
16. K. Shibata, N. Hasegawa, Y. Fukumoto, N. Chatani, ChemCatChem 2012, 4, 1733
17. Y. Aihara, N. Chatani, Chem. Sci. 2013, 4, 664.
18. B. V. S. Reddy, L. R. Reddy, E. J. Corey, Org. Lett. 2006, 8, 3391
19. Y. Feng, G. Chen, Angew. Chem. 2010, 122, 970
20. Angew. Chem. Int. Ed. 2010, 49, 958
21. Y. Feng, Y. Wang, B. Landgraf, S. Liu, G. Chen, Org. Lett. 2010, 12, 3414
22. G. He, G. Chen, Angew. Chem. 2011, 123, 5298
23. Angew. Chem. Int. Ed. 2011, 50, 5192
24. W. R. Gutekunst, P. S. Baran, J. Am. Chem. Soc. 2011, 133, 19076
25. W. R. Gutekunst, R. Gianatassio, P. S. Baran, Angew. Chem. 2012, 124, 7625
26. Angew. Chem. Int. Ed. 2012, 51, 7507
27. G. He, Y. Zhao, S. Zhang, C. Lu, G. Chen, J. Am. Chem. Soc. 2012, 134, 3
28. S.-Y. Zhang, G. He, Y. Zhao, K. Wright, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2012, 134, 7313
29. G. He, C. Lu, Y. Zhao, W. A. Nack, G. Chen, Org. Lett. 2012, 14, 2944
30. Y. Zhao, G. He, W. A. Nack, G. Chen, Org. Lett. 2012, 14, 2948.
31. Recently, Chatani reported a nickel-catalyzed oxidative cycloaddition involving C-H bond cleavage with double coordination assistance:, H. Shiota, Y. Ano, Y Aihara, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 14952.
32. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359
33. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651.
34. C.-Y. He, Q.-Q. Min, X. Zhang, Organometallics 2012, 31, 1335
35. M. Khoobi, M. Alipour, S. Zarei, F. Jafarpour, A. Shafiee, Chem. Commun. 2012, 48, 2985
36. K. H. Kim, H. S. Lee, S. H. Kim, J. N. Kim, Tetrahedron Lett. 2012, 53, 2761
37. J. Shao, W. Chen, M. A. Giulianotti, R. A. Houghten, Y. Yu, Org. Lett. 2012, 14, 5452
38. G. Wu, J. Zhou, M. Zhang, P. Hu, W. Su, Chem. Commun. 2012, 48, 8964
39. J. Dong, Y. Huang, X. Qin, Y. Cheng, J. Hao, D. Wan, W. Li, X. Liu, J. You, Chem. Eur. J. 2012, 18, 6158; see the Supporting Information for complete citations.
40. J. Wencel-Delord, C. Nimphius, F. W. Patureau, F. Glorius, Angew. Chem. 2012, 124, 2290
41. Angew. Chem. Int. Ed. 2012, 51, 2247
42. K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura, Angew. Chem. 2012, 124, 5455
43. Angew. Chem. Int. Ed. 2012, 51, 5359
44. N. Kuhl, M. N. Hopkinson, F. Glorius, Angew. Chem. 2012, 124, 8354
45. Angew. Chem. Int. Ed. 2012, 51, 8230
46. J. Wencel-Delord, C. Nimphius, H. Wang, F. Glorius, Angew. Chem. 2012, 124, 13175
47. Angew. Chem. Int. Ed. 2012, 51, 13001
48. J. Dong, D. Long, F. Song, N. Wu, Q. Guo, J. Lan, J. You, Angew. Chem. 2013, 125, 608
49. Angew. Chem. Int. Ed. 2013, 52, 580
50. X. Qin, H. Liu, D. Qin, Q. Wu, J. You, D. Zhao, Q. Guo, X. Huang, J. Lan, Chem. Sci. 2013, DOI:.
51. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790
52. T. Uemura, S. Imoto, N. Chatani, Chem. Lett. 2006, 35, 842
53. T. Mizuhara, S. Inuki, S. Oishi, M. Fujii, H. Ohno, Chem. Commun. 2009, 3413
54. Q. Shuai, G. Deng, Z. Chua, D. S. Bohle, C.-J. Li, Adv. Synth. Catal. 2010, 352, 632
55. L. Chu, X. Yue, F.-L. Qing, Org. Lett. 2010, 12, 1644
56. W. Wang, F. Luo, S. Zhang, J. Cheng, J. Org. Chem. 2010, 75, 2415.
57. M. Kitahara, N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2011, 133, 2160
58. M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2012, 124, 7099
59. Angew. Chem. Int. Ed. 2012, 51, 6993; also see
60. K. Hirano, M. Miura, Chem. Commun. 2012, 48, 10704.
61. Z. Mao, Z. Wang, Z. Xu, F. Huang, Z. Yu, R. Wang, Org. Lett. 2012, 14, 3854
62. S. Fan, Z. Chen, X. Zhang, Org. Lett. 2012, 14, 4950
63. X. Qin, B. Feng, J. Dong, X. Li, Y. Xue, J. Lan, J. You, J. Org. Chem. 2012, 77, 7677.
64. During the preparation of this manuscript, Daugulis reported a copper-mediated sulfenylation of C sp 2 -H bond with the same bidentate coordination group:, L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 18237.
65. X. A. Domínguez, G. de La Fuente, A. G. Gonzalez, M. Reina, I. Timon, Heterocycles 1988, 27, 35
66. T. Ichiba, W. Y. Yoshida, P. J. Scheuer, T. Higa, D. G. Gravalos, J. Am. Chem. Soc. 1991, 113, 3173
67. E. Selva, G. Beretta, N. Montanini, G. S. Saddler, B. P. Gastaldo, P. Ferrari, R. Lorenzetti, P. Landini, F. Ripamonti, B. P. Goldstein, M. Berti, L. Montanaro, M. Denaro, J. Antibiot. 1991, 44, 693
68. J. Kettenring, L. Colombo, P. Ferrari, P. Tavecchia, M. Nebuloni, K. Vekey, G. G. Gallo, E. Selva, J. Antibiot. 1991, 44, 702
69. A. Nagatsu, H. Kajitani, J. Sakakibara, Tetrahedron Lett. 1995, 36, 4097.
70. For pKa values of representative heteroarenes, see:, K. Shen, Y. Fu, J.-N. Li, L. Liu, Q.-X. Guo, Tetrahedron 2007, 63, 1568.
71. A. J. Mota, A. Dedieu, C. Bour, J. Suffer, J. Am. Chem. Soc. 2005, 127, 7171
72. D. García-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066
73. M. Lafrance, C. N. Rowley, T. K. Woo, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 8754
74. D. Lapointe, K. Fagnou, Chem. Lett. 2010, 39, 1118, and references therein.
75. H.-G. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404
76. L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett. 2008, 10, 3081
77. S. Yotphan, R. G. Bergman, J. A. Ellman, Org. Lett. 2009, 11, 1511
78. D. Zhao, W. Wang, F. Yang, J. Lan, L. Yang, G. Gao, J. You, Angew. Chem. 2009, 121, 3346
79. Angew. Chem. Int. Ed. 2009, 48, 3296
80. T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 3072
81. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900
82. L. Zhang, J. Cheng, T. Ohishi, Z. Hou, Angew. Chem. 2010, 122, 8852
83. Angew. Chem. Int. Ed. 2010, 49, 8670, and references therein.
84. III intermediates, see:, A. Casitas, M. Canta, M. Solá, M. Costas, X. Ribas, J. Am. Chem. Soc. 2011, 133, 19386, and references therein. However, the detailed mechanism of C-H cleavage of 1 a is not clear at this stage.
85. L. M. Huffman, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 9196
86. A. E. King, T. C. Brunold, S. S. Stahl, J. Am. Chem. Soc. 2009, 131, 5044
87. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068.
88. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2009, 131, 17052
89. D. Monguchi, A. Yamamura, T. Fujikawa, T. Somete, A. Mori, Tetrahedron Lett. 2010, 51, 850
90. M. Zhu, K.-i. Fujita, R. Yamaguchi, Chem. Commun. 2011, 47, 12876.
91. Because of the possibility of an off-cycle C-H cupration of 1,3-azoles, at the present, we cannot completely exclude an alternative pathway that includes: 1) formation of an arylcopper species through double N,N-N,N-coordination assistance, 2) insertion of the C=N bond of 1,3-azoles into the C-Cu bond, and 3) oxidation leading to rearomatization of azole cores. Also see:, S. Ranjit, R. Lee, D. Heryadi, C. Shen, J. Wu, P. Zhang, K.-W. Huang, X. Liu, J. Org. Chem. 2011, 76, 8999.