β-hydride elimination in palladium-catalyzed reactions

Chinese Journal of Organic Chemistry

Volumn 25, Issue 10, 2005, Pages 1182-1197

  Han, Xiu Ling ^a   Liu, Gui Xia ^a   Lu, Xi Yan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

heteroatom elimination; hydride elimination; Cross coupling reaction; Palladium(II) catalyzed reaction; Protonolysis

Indexed keywords

EID: 29144527540     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (108)

1. Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Veerlag, Berlin, 1980.
2. Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, New York, 1995.
3. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
4. Tamao, K.; Sumitani, K.; Kumada, M. J. Am Chem. Soc. 1972, 94, 4374.
5. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
6. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998.
7. Tamao, K.; Hiyama, J.; Negishi, E. Special Volume of Thirty Years of the Cross-Coupling Reaction, J. Organomet. Chem. 2002, 653, pp. 1-160.
8. Wilkinson, G Science 1974, 185, 109.
9. Yamamoto, A. Organotransition Metal Chemistry-Fundamental Concepts and Applications, Translated by Chen, H. L.; Lu, X. Y., John Wiley & Sons, New York, 1986, p. 361 (in Chinese).
10. Yamamoto, A. Organotransition Metal Chemistry-Fundamental Concepts and Applications, Translated by Chen, H. L.; Lu, X. Y., John Wiley & Sons, New York, 1986, p. 332 (in Chinese).
11. Cotton, F. A, Chem. Rev. 1955, 55, 551.
12. Taube, R.; Drevs, H.; Steinborn, D. Z. Chem. 1978, 18, 425.
13. Soderberg, B. C. In Comprehensive Organometallic Chemistry II, Vol. 12, Eds.: Abel, E. W.; Stone, F. G. A.; Wilkinson, J., Pergamon, New York, 1995, Ch. 3.5, p. 241.
14. Tsuji, J. Perspectives in Organopalladium Chemistry for the XXI Gentry, Elsevier, Amsterdam, 1999.
15. Mailtis, P. M. The Organic Chemistry of Palladium, Vol. 1-2, Acdemic Press, New York, 1971.
16. Mailtis, P. M. Acc. Chem. Res. 1976, 9, 93.
17. Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
18. Lambert, C.; Utimoto, K.; Nozaaki, H. Tetrahedron Lett. 1984, 25, 5323.
19. Lu, X.; Ma, S.; Zhu, G. Synlett 1998, 115.
20. Lu, X.; Ma, S. In Transition Metal Catalyzed Reaction, Eds.: Murahashi, S. I.; Davis, S. G. Blackwell Science, Oxford, 1999, Ch. 6, p. 133.
21. Wang, Z.; Lu, X. Chem. Commun. 1996, 535.
22. Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
23. Wang, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 5213.
24. Wang, Z.; Lu, X.; Lei, A.; Zhang, Z. J. Org. Chem. 1998, 63, 3806.
25. Wang, Z.; Zhang, Z.; Lu, X. Organometallics 1997, 19, 775.
26. Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
27. Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
28. Jeffery, T. Tetrahedron 1996, 52, 10113.
29. Cacchi, S.; Fabrizi, C.; Marinelli, F.; Moro, L.; Pace, P. Tetrahedron 1996, 52, 10225.
30. Jeffery, T.; Galland, J. C. Tetrahedron Lett. 1994, 35, 4103.
31. Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
32. Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991.
33. Loupy, A.; Tchoubar, B. Salt Effects in Organic and Organometallic Chemistry, VCH, Weiheim, 1992, pp. 254-272.
34. Simone, D. O.; Kennelly, T.; Brungard, N. L.; Farrauto, R. J. Appl. Catal. 1991, 70, 87.
35. Widenhoefer, R. A.; Buchwald, S. L. Organometallics 1996, 15, 2755.
36. Bäckvall, J. E.; B. Äkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411.
37. Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393.
38. Francis, J. W.; Henry, P. M. J. Mol. Catal. A: Chem. 1955, 99, 77.
39. Harrington, P. J. In Comprehensive Organometallic Chemistry II, Vol. 12, Eds.: Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Pergamon, New York, 1995, p. 797, p. 904.
40. Bäckvall, J. E In Metal-Catalyzed Cross-Coupling Reactions, Eds.: Diederich, F.; Stang, P. J., Wiley-VCH, Weinheim, 1998, pp. 339-385.
41. Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
42. Yagupsky, G; Mowat, W.; Shortland, A.; Wilkinson, G. J. Chem. Soc., Chem. Commun. 1970, 1369.
43. Cross, R. J. In The Chemistry of the Metal-Carbon Bond, Vol. 2, Eds.: Hartley, F. R.; Patai, S., Wiley, Chichester, 1985, p. 559.
44. Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometallics 2001, 20, 3724.
45. Zhu, G.; Lu, X. Organometallics 1995, 14, 4899.
46. Yamamoto, A. Organotransition Metal Chemistry, Wiley, New York, 1986, p. 233.
47. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed., University Science Books, Mill Valley, California, 1987.
48. Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120.
49. Lu, X.; Zhu, G.; Ma, S. Tetrahedron Lett. 1992, 33, 7205.
50. Wakabayashi, T.; Ishii, Y.; Murata, T.; Mizobe, Y.; Hidai, M. Tetrahedron Lett. 1995, 36, 5585.
51. Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
52. Zhang, Q.; Lu, X.; Han, X. J. Org. Chem. 2001, 66, 7676.
53. Hegedus, L. S. In Compprensive Organic Synthesis, Vol. 4, Eds.: Trost, B. M.; Fleming, M., Pergamon Press, Oxford, 1991, p. 571.
54. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, Harper and Row, New York, 1987, p. 162.
55. Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis, Vol. 1, Eds.: Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, pp. 283-324.
56. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 8364.
57. Zhao, L.; Lu, X. Org. Lett. 2002, 4, 3903.
58. Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343.
59. Xie, X.; Lu, X.; Liu, Y.; Xu, W. J. Org. Chem. 2001, 66, 6545.
60. Lei, A.; Lu, X. Org. Lett. 2000, 2, 2357.
61. Lei, A.; Liu, G.; Lu, X. J. Org. Chem. 2002, 67, 974.
62. Liu, G.; Lu, X. Tetrahedron Lett. 2002, 43, 6791.
63. Liu, G.; Lu, X. Tetrahedron Lett. 2003, 44, 467.
64. Xie, X.; Lu, X. Synlett 2000, 707.
65. Liu, G.; Lu, X. Tetrahedron Lett. 2003, 44, 127.
66. Liu, G.; Lu, X. Org. Lett. 2001, 3, 3879.
67. Lei, A.; Lu, X. Org. Lett. 2000, 2, 2699.
68. Xie, X.; Lu, X.; Liu, G. Chin. J. Chem. 2001, 19, 1285.
69. Bäckvall, J. E.; Nystrom, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676.
70. Netherton, M. R.; Dai, C.; Neuschutz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
71. Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 47, 1945.
72. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
73. Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187.
74. Cardenas, D. J. Angew. Chem., Int. Ed. 1999, 38, 3018.
75. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
76. Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910.
77. Devasagayaraj, A.; Studemann T.; Knochel, P. Angew. Chem., Int. Ed. 1995, 34, 2723.
78. Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79.
79. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527.
80. Terao, J.; Watanabe, H.; Ikumi, A.; Kumiyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
81. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
82. Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718.
83. Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079.
84. Lee, J.-Y.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 5616.
85. Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642.
86. Wiskur, S. L.; Korte, A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 82.
87. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340.
88. Prim, D.; Campagne, J.-M.; Joseph D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
89. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 1995, 64, 1348.
90. Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 21, 3609.
91. Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626.
92. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
93. Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
94. Paluki, M.; Wolfe, P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395.
95. Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770.
96. Negishi, E.; Ma, S.; Amanfu, J.; Coperet, C.; Miller, J. A.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5919.
97. Coperet, C.; Negishi, E. Org. Lett. 1999, 1, 165.
98. Oh, C. H.; Rhim, C. Y.; Kang, J. H.; Kim, A.; Park, B. S.; Seo, Y. Tetrahedron Lett. 1996, 37, 8875.
99. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. 1999, 38, 1452.
100. Solé, D.; Cancho, Y.; Llebaria, A.; Moletó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133.
101. Giovannini, R.; Stüdemann, T.; Dissin, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 2387.
102. Giovannini, R.; Knochel, P. J. Am. Chem. Soc. 1998, 120, 11186.
103. Divasagayaraj, A.; Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. 1995, 34, 2723.
104. Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79.
105. Lee, C.-W.; Oh, K. S.; Kim, K. S.; Ahn, K. H. Org. Lett. 2000, 2, 1213.
106. Aggarwal, V. K.; Daries, P. W.; Moss, W. O. Chem. Commun. 2002, 972.