Copper-catalyzed oxidative cross-coupling of N,N-Dimethylanilines with heteroarenes under molecular oxygen

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1759-1766

  Huang, Lehao ^a   Niu, Tianmin ^a   Wu, Jun ^a   Zhang, Yuhong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER CATALYST; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; HETEROARENES; HETEROCYCLES; HETEROCYCLIC COMPOUND; INDOLIZINES; MILD REACTION CONDITIONS; SYNTHETIC METHODS;

CATALYSTS; CHEMICAL REACTIONS; FUNCTIONAL MATERIALS;

MOLECULAR OXYGEN;

ANILINE; ANILINE DERIVATIVE; COPPER; IMIDAZOLE; INDOLE; INDOLIZINE DERIVATIVE; N,N DIMETHYLANILINE; OXYGEN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; OXIDATION;

EID: 79952633971     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1023975     Document Type: Article

References (104)

1. For representative reviews, see: (a) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
2. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
3. (c) Godula, K.; Sames, D. Science 2006, 312, 67.
4. (d) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
5. (e) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
6. (f) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
7. (g) Ackermann, L. Chem. Commun. 2010, 4866.
8. (h) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
9. (i) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654.
10. (j) Lu, H.; Zhang, X. P. Chem. Soc. Rev. DOI: 10.1039/c0cs00070a.
11. For representative references, see: (a) Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
12. (b) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
13. (c) Maleczka, R. E., Jr. Science 2009, 323, 1572.
14. (d) Zhou, H.; Xu, Y.-H.; Chung, W.-J.; Loh, T.-P. Angew. Chem., Int. Ed. 2009, 48, 5355.
15. (e) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
16. (f) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
17. (g) Baslé , O.; Li, C.-J. Org. Lett. 2008, 10, 3661.
18. (h) Chaumontet, M.; Piccardi, R.; Audic, N.; Hitce, J.; Peglion, J.-L.; Clot, E.; Baudoin, O. J. Am. Chem. Soc. 2008, 130, 15157.
19. (i) Nakao, Y.; Kashihara, N.; Kanyiva, K. S.; Hiyama, T. Angew. Chem., Int. Ed. 2010, 49, 4451.
20. (j) Kumaraswamy, G.; Murthy, A. N.; Pitchaiah, A. J. Org. Chem. 2010, 75, 3916.
21. (k) Ye, X.; Xie, C.; Pan, Y.; Han, L.; Xie, T. Org. Lett. 2010, 12, 4240.
22. (l) Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2007, 9, 3813.
23. For representative reviews, see: (a) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
24. (b) Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540.
25. (c) Klussmann, M.; Sureshkumar, D. Synthesis 2010. DOI: 10.1055/ s-0030-1258303.
26. (d) Scheuermann, C. J. Chem. Asian J. 2010, 5, 436.
27. For representative references, see:(e) Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709.
28. (f) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
29. (g) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904.
30. (h) Dohi, T.; Ito, M.; Morimoto, K.; Iwata, M.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 1301.
31. (i)Zhao, X.; Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 5837.
32. (j) Xi, P.; Yang, F.; Qin, S.; Zhao, D.; Lan, J.; Gao, G.; Hu, C.; You, J. J. Am. Chem. Soc. 2010, 132, 1822.
33. (k) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.
34. (l) Yang, Y.; Cheng, K.; Zhang, Y. Org. Lett. 2009, 11, 5606.
35. (m) Li, Z.; Yu, R.; Li, H. Angew. Chem., Int. Ed. 2008, 47, 7497.
36. (n) Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512.
37. (o) Richter, H.; Mancheño, O. G. Eur. J. Org. Chem. 2010, 4460.
38. For representative references of CDC transformations with tertiary amines, see: (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
39. (b) Sud, A.; Sureshkumar, D.; Klussmann, M. Chem. Commun. 2009, 3169.
40. (c) Jovel, I.; Prateeptongkum, S.; Jackstell, R.; Vogl, N.; Weckbeckerb, C.; Beller, M. Chem. Commun. 2010, 1956.
41. (d) Han, W.; Ofial, A. R. Chem. Commun. 2009, 6023.
42. (e) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
43. (f) Ohta, M.; Quick, M. P.; Yamaguchi, J.;Wü nsch, B.; Itami, K. Chem. Asian J. 2009, 4, 1416.
44. (g) Liu, P.; Zhou, C.-Y.; Xiang, S.; Che, C.-M. Chem. Commun. 2010, 2739.
45. (h) Yang, F.; Li, J.; Xie, J.; Huang, Z.-Z. Org. Lett. 2010, 12, 5214.
46. (i) Shirakawa, E.; Uchiyama, N.; Hayashi, T. J. Org. Chem. 2011, 76, 25.
47. (j) Shen, Y.; Li, M.; Wang, S.; Zhan, T.; Tan, Z.; Guo, C.-C. Chem. Commun. 2009, 953.
48. (k) Baslé , O.; Li, C.-J. Chem. Commun. 2009, 4124.
49. (l) Baslé , O.; Li, C.-J. Green Chem. 2007, 9, 1047.
50. (m) Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. J. Chem. Res, Synop. 1993, 434.
51. (n) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672.
52. (o) Baslé , O.; Borduas, N.; Dubois, P.; Chapuzet, J. M.; Chan, T.-H.; Lessard, J.; Li, C.-J. Chem.-Eur. J. 2010, 16, 8162.
53. (p) Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075.
54. (q) Rao Volla, C. M.; Vogel, P. Org. Lett. 2009, 11, 1701.
55. (a) Deng, G.; Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 6278.
56. (b) Deng, G.; Li, C.-J. Org. Lett. 2009, 11, 1171.
57. (c) Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817.
58. (d) Rong, Y.; Li, R.; Lu, W. Organometallics 2007, 26, 4376.
59. (a) Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.
60. (b) Hatamoto, Y.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2004, 6, 4623.
61. (c) Brasche, G.; Garcí a-Fortanet, J. S.; Buchwald, L. Org. Lett. 2008, 10, 2207.
62. (d) Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115.
63. (e) Yoo, W.-J.; Correia, C. A.; Zhang, Y.; Li, C.-J. Synlett 2009, 138.
64. (f) King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068.
65. (g) Pinté r, á .; Sud, A.; Sureshkumar, D.; Klussmann, M. Angew. Chem., Int. Ed. 2010, 49, 5004.
66. (h) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
67. (i) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
68. (j) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
69. (k) Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.
70. (l) Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842.
71. (m) Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11, 1607.
72. (n) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
73. (o) Gao, Y. X.; Wang, G.; Chen, L.; Xu, P. X.; Zhao, Y. F.; Zhou, Y. B.; Han, L. B. J. Am. Chem. Soc. 2009, 131, 7956.
74. (p) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2009, 131, 17052.
75. (q) Wie, Y.; Zhao, H.; Kann, J.; Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522.
76. (r) Niu, T.; Zhang, Y. Tetrahedron Lett. 2010, 51, 6847.
77. (s) Kitahara, M.; Hirano, K.; Tsurugi, H.; Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 1772.
78. (t) Yang, L.; Zhao, L.; Li, C.-J. Chem. Commun. 2010, 4184.
79. (a) Murata, S.; Miura, M.; Nomura, M. J. Chem. Soc., Chem. Commun. 1989, 116.
80. (b) Murata, S.; Miura, M.; Nomura, M. J. Org. Chem. 1989, 54, 4700.
81. (c) Lié gault, B.; Fagnou, K. Organometallics 2008, 27, 4841.
82. (d) Andrews, P. C.; Junk, P. C.; Kemppinen, K. P.; Konstas, K.; Tuck, K. L. Lett. Org. Chem. 2009, 6, 229.
83. (e) Klein, J. E. M. N.; Perry, A.; Pugh, D. S.; Taylor, R. J. K. Org. Lett. 2010, 12, 3446.
84. (a) Cytochrome P-450, Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995.
85. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; pp 387-397.
86. (c) Murahashi, S.-I.; Zhang, D. Chem. Soc. Rev. 2008, 37, 1490.
87. (d) Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069.
88. (a) Chiavarino, B.; Cipollini, R.; Crestoni, M. E.; Fornarini, S.; Lanucara, F.; Lapi, A. J. Am. Chem. Soc. 2008, 130, 3208.
89. (b) Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312.
90. (c) Murahashi, S.-I.; Naota, T.; Yonemura, K. J. Am. Chem. Soc. 1988, 110, 8256.
91. (d) Sureshkumar, D.; Sud, A.; Klussmann, M. Synlett 2009, 1558.
92. Huang, L.; Zhang, X.; Zhang, Y. Org. Lett. 2009, 11, 3730.
93. (a) Howe, E. E.; Zambito, A. J.; Snyder, H. R.; Tishler, M. J. Am. Chem. Soc. 1945, 67, 38.
94. (b) Albright, J. D.; Snyder, H. R. J. Am. Chem. Soc. 1959, 81, 2239.
95. (c) Iwao, M.; Motoi, O. Tetrahedron Lett. 1995, 36, 5929.
96. (d) Chauder, B.; Larkin, A.; Snieckus, V. Org. Lett. 2002, 4, 815.
97. (e) Herrá n, G.; Segura, A.; Csákÿ, A.G. Org. Lett. 2007, 9, 961.
98. (f) Li,H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176.
99. (a) Li, H.; Xia, Z.; Chen, S.; Koya, K.; Ono, M.; Sun, L. Org. Process Res. Dev. 2007, 11, 246.
100. (b) Zhou, H.; Danger, D. P.; Dock, S. T.; Hawley, L.; Roller, S. G.; Smith, C. D.; Handlon, A. L. ACS Med. Chem. Lett. 2010, 1, 19.
101. For representative reviews, see: (a) Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.
102. (b) Kochanowska-Karamyan, A.-J.; Hamann, M.-T. Chem. Rev. 2010, 110, 4489.
103. Zhang, L.; Liang, F.; Sun, L.; Hu, Y.; Hu, H. Synthesis 2000, 1733.
104. Pollak, I. E.; Grillot, G. F. J. Org. Chem. 1967, 32, 2892.