Ni-catalyzed C(sp2)-carbon and C(sp2)-heteroatom cross-coupling reactions

Chinese Journal of Organic Chemistry

Volumn 25, Issue 12, 2005, Pages 1508-1529

  Li, Zhe ^a   Fu, Yao ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Catalytic reaction; Cross coupling; Ni; Reaction mechanism

Indexed keywords

EID: 32044466267     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (123)

1. (a) Diederich, F.; Stang, P. J. Metal-catalyzed Cross-coupling Reactions, Wiley-VCH, Weinheim, 1998.
2. (b) Baranano, D.; Mann, G; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
3. (c) Cheng, Q.-F.; Jiang, C.-S.; You, T.-P. Chin. J. Org. Chem. 2001, 21, 173 (in Chinese).
4. (d) Zhang, Z.-F.; Zhou, W.-C. Chin. J. Org. Chem. 2002, 22, 685 (in Chinese).
5. (e) Bedford, R. B. Chem. Commun. 2003, 1787.
6. (f) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566.
7. (f) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
8. (g) Lu, X.-Y.; Du, C.-P. Reaction Chemistry of Organametallic Compound, Chemical Industry Press, Beijing, 2002 (in Chinese).
9. Kharasch, M. S.; Reinmuth, O. Grignard Reagents of Nonmetallic Substances, Prentice-Hall Inc., New York, 1954.
10. Tamura, M.; Kochi, J. J. Am. Chem. Soc. 1971, 93, 1487.
11. Uchino, M.; Yamamoto, A.; Ikeda, S. J. Organomet. Chem. 1970, 24, C63.
12. Corriu, R. J. P.; Masse, J. P. Chem. Commun. 1972, 144.
13. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
14. Negishi, E. I. J. Organomet. Chem. 2002, 653, 34.
15. Murahashi, S. I.; Davies, S. G. Transition Metal Catalyzed Reactions, Lackwell Science, 1999.
16. (a) Mizoraki, T.; Mon, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
17. (b) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 14, 2320.
18. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
19. (b) Wang, Z.-Y.; Zhang, Z.-D.; Li, Q.-R.; Guo, Q.-X. Chem. J. Chin. Univ. 2002, 23, 58 (in Chinese).
20. Hou, J.-J.; Yang, L.-R.; Cui, X.-L.; Wu, Y.-J. Chin. J. Chem. 2003, 21, 717.
21. (b) Zheng, R.; Yang, F.; Zou, G.; Tang, J.; He, M.-Y. Chin. J. Chem. 2003, 21, 1111.
22. Liu, P.; Wang, L.; Li, L.-M.; Wang, X.-Y. Chin. J. Org. Chem. 2004, 24, 59 (in Chinese).
23. Ma, S.-M. Metal Involved Modern Synthetic Organic Reactions, Guangdong Science and Techology Press, Guangzhou, 2001 (in Chinese).
24. Boldrini, G. P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Ronchi, A. U. J. Organomet. Chem. 1986, 301, C62.
25. Iyer, S.; Ramesh, C.; Ramani, A. Tetrahedron Lett. 1997, 38, 8533.
26. Bhanage, B. M.; Zhao, F. G; Shirai, M.; Arai, M. Tetrahedron Lett. 1998, 39, 9509.
27. Bhanage, B. M.; Zhao, F.; Shirai, M.; Arai, M. Catal. Lett. 1998, 54, 195.
28. (a) Wang, L.; Li, P.-H. Chin. J. Chem. 2003, 21, 474.
29. (b) Xia, M.; Wang, Y.-G. Chin. J. Org. Chem. 2003, 23, 609 (in Chinese).
30. Beletskaya, I. P.; Latyshev, G. V.; Tsvetkov, A. V.; Lukashev, N. V. Tetrahedron Lett. 2003, 44, 5011.
31. Wang, L.; Li, P.; Zhang, Y. Chem. Commun. 2004, 514.
32. (a) Li, L.-T.; Ma, S.-M. Chin. J. Org. Chem. 2001, 21, 75 (in Chinese).
33. (b) Tamao, K. J. Organometal. Chem. 2002, 653, 23.
34. Consiglio, G.; Morandini, F.; Piccolo, O. Tetrahedron 1983, 39, 2699.
35. Bohm, V. P. W.; Gstottmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387.
36. Mongin, F.; Mojovic, L.; Guillamet, B.; Trecourt, F.; Queguiner, G. J. Org. Chem. 2002, 67, 8991.
37. Miller, J. A. Tetrahedron Lett. 2001, 42, 6991.
38. Miller, J.; Dankwardt, J. Tetrahedron Lett. 2003, 44, 1907.
39. Wenkert, E.; Hanna, M.; Leftin, M.; Michelotti, E. J. Org. Chem. 1985, 50, 1125.
40. Sengupta, S.; Leite, M.; Raslan, D. S.; Quesnelle, C.; Snieckus, V. J. Org. Chem. 1992, 57, 4066.
41. Busacca, C. A.; Eriksson, M. C.; Fiaschi, R. Tetrahedron Lett. 1999, 40, 3101.
42. Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.
43. Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428.
44. Okamura, H.; Miura, M.; Kodugi, K.; Takei, H. Tetrahedron Lett. 1980, 21, 87.
45. Taser, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190.
46. Ikoma, Y.; Taya, F.; Ozald, E.; Higuchi, S.; Naoi, Y. Synthesis 1990, 147.
47. Wang, J. P.; Pomerantz, M. Tetrahedron Lett. 1995, 36, 2571.
48. Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
49. (a) Kosugi, M.; Fugami, K. J. Organomet. Chem. 2002, 653, 50.
50. (b) Liu, F.-S.; Yu, S.-T.; Ge, X.-P.; Yang, J.-Z. Chem. J. Chin. Univ. 2003, 24, 1592 (in Chinese).
51. Shirakawa, E.; Yamasaki, K.; Hiyama, T. J. Chem. Soc., Perkin Trans. 1 1997, 2449.
52. Shirakawa, E.; Yamasaki, K.; Hiyama, T. Synthesis 1998, 1544.
53. Kang, S.; Ryu, H.; Lee, S. J. Chem. Soc., Perkin Trans. 1 1999, 2662.
54. Negishi, E.-I. In Metal-Catalyzed Cross-Coupling Reactions, Eds.: Diederich, F.; Stang, P. J., Wiley-VCH, New York, 1998.
55. Lipshutz, B.; Blomgren, P.; Kim, S. Tetrahedron Lett. 1999, 40, 197.
56. Lipshutz, B.; Blomgren, P. J. Am. Chem. Soc. 1999, 121, 5819.
57. Jensen, A.; Dohle, W.; Knochel, P. Tetrahedron 2000, 56, 4197.
58. Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem., Int. Ed. 2004, 43, 6180.
59. Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1997, 119, 12376.
60. Quesnelle, C. A.; Familone, O. B.; Snieckus, V. Synlett 1994, 349.
61. (a) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
62. (b) Huang, J.; Niu, Y.-H.; Yang, W.; Hou, Q.; Xu, Y.-S.; Yuan, M.; Cao, Y. Acta Chim. Sinica 2003, 61, 765 (in Chinese).
63. (c) huang, Z.-P.; Kung, M.-P.; Ono, M.; Hou, C.; Kung, H. F. Chin. J. Chem. 2003, 21, 824.
64. Zou, Y.; Wang, Q.-R.; Tao, F.-G.; Ding, Z.-B. Chin. J. Chem. 2004, 22, 215.
65. Suzuki, A. J. Organomet. Chem. 2002, 653, 83
66. Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024.
67. Indolese, A. F. Tetrahedron Lett. 1997, 38, 20. 3513.
68. Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8657.
69. Galland, J. C.; Savignac, M.; Genet, J. P. Tetrahedron Lett. 1999, 40, 2323.
70. Zim, D.; Monteiro, A. L. Tetrahedron Lett. 2002, 43, 4009.
71. Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139.
72. Zim, K.; Lando, R. L.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049.
73. Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058.
74. Percec, V.; Bae, J. Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060.
75. Ueda, M.; Saitoh, A.; Saori, O.-T.; Norio, M. Tetrahedron 1998, 54, 13079.
76. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340.
77. Kobayashi, K.; Murugesh, M. G.; Nakano, M.; Takahisa, E.; Usmani, S. B.; Ainai, T. J. Org. Chem. 2002, 67, 7110.
78. Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241.
79. Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
80. (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
81. (b) Qin, C.; Liu, M.; Song, L.-K.; Rong, G.-B. Chin. J. Org. Chem. 2002, 22, 1013 (in Chinese).
82. Takagi, K.; Hayama, N.; Inokawa, S. Bull. Chem. Soc. Jpn. 1980, 53, 3691.
83. Takagi, K.; Hayama, N. Chem. Lett. 1983, 637.
84. Lin, G. Q.; Hong, R. J. Org. Chem. 2001, 66, 2877.
85. Hong, R.; Hoen, R.; Zhang, J.; Lin, G. Q. Synlett 2001, 1527.
86. Chen, C. Synlett 2000, 1490.
87. (a) Fan, X.-S.; Zhang, X.-Y.; Zhang, Y.-M. Chin. J. Chem. 2003, 21, 336.
88. (b) Zheng, X.-L.; Zhang, Y.-M. Chin. J. Chem. 2002, 20, 925.
89. (c) Zhang, J.-M.; Zhang, Y.-M. Chin. J. Chem. 2002, 20, 111.
90. Zheng, X. L.; Zhang, Y. M. J. Chem. Res., Synop. 2002, 562.
91. Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319.
92. (a) Zhang, S.-B.; Ding, M.-X.; Gao, L.-X. Chin. J. Org. Chem. 2002, 22, 159 (in Chinese).
93. (b) Du, D.-M.; Chen, X.; Hua, W.-T. Chin. J. Org. Chem. 2003, 23, 331 (in Chinese).
94. (c) Gu, Y.-L.; Peng, J.-J.; Qiao, K.; Yang, H.-Z.; Shi, F.; Deng, Y.-Q. Prog. Chem. 2003, 15, 222 (in Chinese).
95. Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
96. Desmarets, C.; Schnerder, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 247.
97. Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron 2001, 57, 7657.
98. Brenner, E.; Schnerder, R.; Fort, Y. Tetrahedron Lett. 2000, 47, 2881.
99. Gradel, B.; Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 5689.
100. Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029.
101. Omar-Amrani, R.; Thomas, A.; Brenner, E.; Schneider, R.; Fort, Y. Org. Lett. 2003, 5, 2311.
102. Arterbum, J. B.; Pannala, M.; Gonzalez, A. M. Tetrahedron Lett. 2001,42,1475.
103. Zhao, J. K.; Wang, Y. G. Chin. Chem. Lett. 2002, 13, 1149.
104. Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911.
105. Lipshutz, B. H.; Ueda, H. Angew. Chem., Int. Ed. 2000, 39, 4492.
106. Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413.
107. Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150 (in Chinese).
108. Ager, D. J.; Laneman, S. A. Chem. Commun. 1997, 2359.
109. Budnikova, Y.; Kargin, Y.; Nedelec, J.-Y.; Perichon, J. J. Organomet. Chem. 1999, 575, 63.
110. Beletskaya, I. P.; Afanasiev, V. V.; Kazankova, M. A.; Efimova, I. V. Org. Lett. 2003, 5, 4309.
111. Takagi, K. Chem. Lett. 1985, 1307.
112. Cristau, H. J.; Chabaud, B.; Chene, A.; Christol, H. Synthesis 1981, 892.
113. Foa, M.; Santi, R.; Garabaglia, F. J Organomet. Chem. 1981, 206, C29.
114. Takagi, K. Chem. Lett. 1987, 2221.
115. Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christol, H. J. Org. Chem. 1981, 57, 875.
116. Lin, B.-L.; Liu, L.; Fu, Y.; Luo, S.-W.; Chen, Q.; Quo, Q.-X. Organometallics 2004, 23, 2114.
117. (a) Amatore, C.; Carre, E.; Jutand, A.; M'Barki, M.; Meyer, G. Organometallics 1995, 14, 5605.
118. (b) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
119. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
120. Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547.
121. (a) Cassar, L. J. Organomet. Chem. 1973, 51, 381.
122. (b) Cassar, L.; Foa, M. J. Organomet. Chem. 1974, 54, C57.
123. Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267.