Copper-Catalyzed Ligand Promoted Ullmann-Type Coupling Reactions

Catalysis without Precious Metals

Volumn , Issue , 2010, Pages 213-233

  Jiang, Yongwen ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl amines; Aryl halides; Biaryl ethers; Copper catalysts; Coupling; N,O and N,N bidentate ligands

Indexed keywords

EID: 84878243846     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527631582.ch9     Document Type: Chapter

References (110)

1. For reviews, see: Monnier, F., Taillefer, M. (2008) Angew. Chem. Int. Ed., 47, 3096;
2. Evano, G., Blanchard, N., and Toumi, M. (2008) Chem. Rev., 108, 3054;
3. Finet, J.-P., Fedorov, A.Y., Combes, S., and Boyer, G. (2002) Current Org. Chem., 6, 597;
4. Ley, S.V., and Thomas, A.W. (2003) Angew. Chem. Int. Ed., 42, 5400;
5. Kunz, K., Scholz, U., and Ganzer, D. (2003) Synlett, 2428;
6. Beletskaya, I.P., and Cheprakov, A.V. (2004) Coord. Chem. Rev., 248, 2337.
7. Ma, D., Cai, Q., and Zhang, H. (2003) Org. Lett., 5, 2453.
8. Zhang, H., Cai, Q., and Ma, D. (2005) J. Org. Chem., 70, 5164.
9. Kwong, F.Y., and Buchwald, S.L. (2003) Org. Lett., 5, 793.
10. Kwong, F.Y., Klapars, A., and Buchwald, S.L. (2002) Org. Lett., 4, 581.
11. Shafir, A., and Buchwald, S.L. (2006) J. Am. Chem. Soc., 128, 8742.
12. Shafir, A., Lichtor, P.A., and Buchwald, S.L. (2007) J. Am. Chem. Soc., 129, 3490.
13. Jiang, D., Fu, H., Jiang, Y. and Zhao, Y. (2007) J. Org. Chem., 72, 672.
14. Zhu, D., Wang, R., Mao, J., Xu, L., Wu, F., and Wan, B. (2006) J. Mol. Catal. A:Chem, 256, 256.
15. Goodbrand, H.B., and Hu, N.-X. (1999) J. Org. Chem., 64, 670.
16. Gujadhur, R.K., Bates, C.G., and Venkataraman, D. (2001) Org. Lett., 3, 4315.
17. Guo, X., Rao, H., Fu, H., Jiang, Y., and Zhao, Y. (2006) Adv. Synth. Catal., 348, 2197.
18. Liu, Y., Bai, Y., Zhang, J., Li, Y., Jiao, J., and Qi, X. (2007) Eur.J. Org. Chem., 6084.
19. Altman, R.A., Anderson, K.W., and Buchwald, S.L. (2008) J. Org. Chem., 73, 5167.
20. Lang, F., Zewge, D., Houpis, I.N., and Volante, R.P. (2001) Tetrahedron Lett., 42, 3251.
21. Kim, J., and Chang, S. (2008) Chem. Commun., 3052.
22. Gao, X., Fu, H., Qiao, R., Jiang, Y., and Zhao, Y. (2008) J. Org. Chem., 73, 6864.
23. Kiyomori, A., Marcoux, J.-F., and Buchwald, S.L. (1999) Tetrahedron Lett., 40, 2657.
24. Altman, R.A., and Buchwald, S.L. (2006) Org. Lett., 8, 2779.
25. Altman, R.A., Koval, E.D., and Buchwald, S.L. (2007) J. Org. Chem., 72, 6190.
26. Klapars, A., Antilla, J.C., Huang, X., and Buchwald, S.L. (2001) J. Am. Chem. Soc., 123, 7727.
27. Antilla, J.C., Klapars, A., and Buchwald, S.L. (2002) J. Am. Chem. Soc., 124, 11684.
28. Antilla, J.C., Baskin, J.M., Barder, T.E., and Buchwald, S.L. (2004) J. Org. Chem., 69, 5578.
29. Ma, D., and Cai, Q. (2004) Synlett, 128.
30. Cristau, H.-J., Cellier, P.P., Hamada, S., Spindler, J.-F., and Taillefer, M. (2004) J. Org. Chem., 695.
31. Cristau, H.-J., Cellier, P.P., Hamada, S., Spindler, J.-F., and Taillefer, M. (2004) Chem. Eur. J., 10, 5607.
32. Lv, X., and Bao, W. (2007) J. Org. Chem., 72, 3863.
33. Wang, Z., Bao, W., and Jiang, Y. (2005) Chem. Commun., 2849.
34. Shen, G., Lv, X., Qian, W., and Bao, W. (2008) Tetrahedron Lett., 49, 4556.
35. Taillefer, M., Quali, A., Renard, B., and Spindler, J.-F. (2006) Chem. Eur.J., 12, 5301.
36. Klapars, A., Huang, X., and Buchwald, S.L. (2002) J. Am. Chem. Soc., 124, 7421.
37. Tao, C.-Z., Li, J., Fu, Y., Liu, L., and Guo, Q.-X. (2008) Tetrahedron Lett., 49, 70.
38. Wolter, M., Klapars, A., and Buchwald, S.L. (2001) Org. Lett., 3, 3803.
39. Jones, K.L., Porzelle, A., Hall, A., Woodrow, M.D., and Tomkinson, N.C.O. (2008) Org. Lett., 10, 797.
40. Hosseinzadeh, R., Tajbakhsh, M., Mohadjerani, M., and Mehdinejad, H. (2004) Synlett, 9, 1517.
41. Altman, R.A., and Buchwald, S.L. (2007) Org. Lett., 9, 643.
42. Shen, R., and Porco, J.A. (2000) Org. Lett., 2, 1333.
43. Jiang, L., Job, G.E., Klapars, A., and Buchwald, S.L. (2003) Org. Lett., 5, 3667.
44. Pan, X., Cai, Q., and Ma, D. (2004) Org. Lett., 6, 1809.
45. Han, C., Shen, R., Su, S., and Porco, J.A. (2004) Org. Lett., 6, 27.
46. Frederick, M.O., Mulder, J.A., Tracey, M.R., Hsung, R.P., Huang, J., Kurtz, K.C.M., Shen, L., and Douglas, C.J. (2003) J. Am. Chem. Soc., 125, 2368.
47. Zhang, Y., Hsung, R.P., Tracey, M.R., Kurtz, K.C.M., and Vera, E.L. (2004) Org. Lett., 6, 1151.
48. Istrate, F.M., Buzas, A.K., Jurberg, I.D., Odabachian, Y., and Gagosz, F. (2008) Org. Lett., 10, 925.
49. Zhu, W., and Ma, D. (2004) Chem. Commun., 888.
50. Anderson, J., Madsen, U., Bjorkling, F., and Liang, X. (2005) Synlett, 14, 2209.
51. Anderson, J., Bolvig, S., and Liang, X. (2005) Synlett, 19, 2941.
52. Ackermann, L., Potukuchi, H.K., Landsberg, D., and Vicente, R. (2008) Org. Lett., 10, 3081.
53. Buck, E., Song, Z.J., Tshaen, D., Dormer, P.G., Volane, R.P., and Reider, P.J. (2002) Org. Lett., 4, 1623.
54. Ma, D., and Cai, Q. (2003) Org. Lett., 5, 3799.
55. Cristau, H.-J., Cellier, P.P., Hamada, S., Spindler, J.-F., and Taillefer, M. (2004) Org. Lett., 6, 913.
56. Ouali, A., Spindler, J.-F., Cristau, H.-J., and Taillefer, M. (2006) Adv. Synth. Catal., 348, 499.
57. Cai, Q., He, G., and Ma, D. (2006) J. Org. Chem., 71, 5268.
58. Quali, A., Splindler, J.-F., Jutand, A., and Taillefer, M. (2007) Adv. Synth. Catal., 349, 1906.
59. Xia, N., and Taillefer, M. (2008) Chem. Eur. J., 14, 6037.
60. Cai, Q., Zou, B., and Ma, D. (2006) Angew. Chem. Int. Ed., 45, 1276.
61. Ma, D., Cai, Q., and Xie, X. (2005) Synlett, 11, 1767.
62. Wolter, M., Nordmann, G., Job, G.E., and Buchwald, S.L. (2002) Org. Lett., 4, 973.
63. Hosseinzadeh, R., Tajbakhsh, M., Mohadjerani, M., and Alikarami, M. (2005) Synlett, 7, 1101.
64. Altman, R.A., Shafir, A., Choi, A., Lichtor, P.A., and Buchwald, S.L. (2008) J. Org. Chem., 73, 284.
65. Zhang, H., Ma, D., and Cao, W. (2007) Synlett, 243.
66. Job, G.E., and Buchwald, S.L. (2002) Org. Lett., 4, 3703.
67. Ma, D., and Liu, F. (2004) Chem. Commun., 1934.
68. Mao, J., Guo, J., and Ji, S. (2008) J. Mol. Catal. A:Chem., 284, 85.
69. Liu, F., and Ma, D. (2007) J. Org. Chem., 72, 4844.
70. Bates, C.G., Saejueng, P., and Venkataraman, D. (2004) Org. Lett., 6, 1441.
71. Hennessy, E.J., and Buchwald, S.L. (2002) Org. Lett., 4, 269.
72. Xie, X., Cai, G., and Ma, D. (2005) Org. Lett., 7, 4693.
73. Jiang, Y., Wu, N., Wu, H., and He, M. (2005) Synlett, 18, 2731.
74. Yip, S.F., Cheung, H.Y., Zhou, Z., and Kwong, F.Y. (2007) Org. Lett., 9, 3469.
75. Xie, X., Chen, Y., and Ma, D. (2006) J. Am. Chem. Soc., 128, 16050.
76. Zanon, J., Klapars, A., and Buchwald, S.L. (2003) J. Am. Chem. Soc., 125, 2890.
77. Cristau, H.-J., Ouali, A., Spindler, J.-F., and Taillefer, M. (2005) Chem. Eur.J., 11, 2483.
78. Wang, D., Kuang, L., Li, Z., and Ding, K. (2008) Synlett, 69.
79. Bates, C.G., Gujadhur, R.K., and Venkataraman, D. (2002) Org. Lett., 4, 2803.
80. Kwong, F.Y., and Buchwald, S.L. (2002) Org. Lett., 4, 3517.
81. Deng, W., Zou, Y., Wang, Y.-F., Liu, L., and Guo, Q.-X. (2004) Synlett, 7, 1254.
82. Zhang, H., Cao, W., and Ma, D. (2007) Syn. Commun., 37, 25.
83. Bates, C.G., Saejueng, P., Doherty, M.Q., and Venkataraman, D. (2004) Org. Lett., 6, 5005.
84. Zheng, Y., Du, X., and Bao, W. (2006) Tetrahedron Lett., 47, 1217.
85. Wang, Z., Mo, H., and Bao, W. (2007) Synlett, 91.
86. Kabir, M.S., Van Linn, M.L., Monte, A., and Cook, J.M. (2008) Org. Lett., 10, 3363.
87. Zhu, W., and Ma, D. (2005) J. Org. Chem., 70, 2696.
88. Baskin, J.M., and Wang, Y. (2002) Org. Lett., 4, 4423.
89. Allen, D.V., and Venkataraman, D. (2003) J. Org. Chem., 68, 4590.
90. Gelman, D., Jiang, L., and Buchwald, S.L. (2003) Org. Lett., 5, 2315.
91. Huang, C., Tang, X., Fu, H., Jiang, Y., and Zhao, Y. (2006) J. Org. Chem., 71, 5020.
92. For selected examples, see: Yuan, Q., Ma, D. (2008) J. Org. Chem., 73, 5159;
93. Chen, Y., Wang, Y., Sun, Z., and Ma, D. (2008) Org. Lett., 10, 625;
94. Wang, B., Lu, B., Jiang, Y., Zhang, Y., and Ma, D. (2008) Org. Lett., 10, 2761;
95. Minatti, A., and Buchwald, S.L. (2008) Org. Lett., 10, 2721;
96. Viirre, R.D., Evindar, G., and Batey, R.A. (2008) J. Org. Chem., 73, 3452;
97. Yang, D., Fu, H., Hu, L., Jiang, Y., and Zhao, Y. (2008) J. Org. Chem., 73, 7841;
98. Bao, W., Liu, Y., Lv, X., and Qian, W. (2008) Org. Lett., 10, 3899;
99. Lu, B., Wang, B., Zhang, Y., and Ma, D. (2007) J. Org. Chem., 72, 5337;
100. Zou, B., Yuan, Q., and Ma, D. (2007) Angew. Chem. Int. Ed., 46, 2598;
101. Zou, B., Yuan, Q., and Ma, D. (2007) Org. Lett., 9, 4291;
102. Chen, Y., Xie, X., and Ma, D. (2007) J. Org. Chem., 72, 9329;
103. Zheng, N., and Buchwald, S.L. (2007) Org. Lett., 9, 4749;
104. Rivero, M.R., and Buchwald, S.L. (2007) Org. Lett., 9, 973;
105. Martín, R., Cuenca, A., and Buchwald, S.L. (2007) Org. Lett., 9, 5521;
106. Jones, C.P., Anderson, K.W., and Buchwald, S.L. (2007) J. Org. Chem., 72, 7968;
107. Yuan, X., Xu, X., Zhou, X., Yuan, J., Mai, L., and Li, Y. (2007) J. Org. Chem., 72, 1510-1513;
108. Martin, R., Rodriguez, R., and Buchwald, S.L. (2006) Angew. Chem. Int. Ed., 45, 7079;
109. Klapars, A., Parris, S., Andersom, K.W., and Buchwald, S.L. (2004) J. Am. Chem. Soc., 126, 3529;
110. Bates, C.G., Saejueng, P., Murphy, J.M., and Venkataraman, D. (2002) Org. Lett., 4, 4727.