A quarter of a century of explorations in organozirconium chemistry

Dalton Transactions

Volumn , Issue 5, 2005, Pages 827-848

  Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; DERIVATIVES; OLEFINS; OXIDATION; QUENCHING; STOICHIOMETRY; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CARBON-CARBON BOND-FORMING REACTIONS; HYDROBORATION; INSERTION REACTIONS; ORGANOZIRCONIUM CHEMISTRY;

ORGANOMETALLICS;

ORGANOMETALLIC COMPOUND; ZIRCONIUM;

ARTICLE; CHEMISTRY; HISTORY;

HISTORY, 20TH CENTURY; HISTORY, 21ST CENTURY; ORGANOMETALLIC COMPOUNDS; ZIRCONIUM;

EID: 15244341482     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417134a     Document Type: Article

References (235)

1. J. J. Bergelius, Am. Chim. Phys., 1824, 26, 43.
2. G. Wilkinson and J. M. Birmingham, J. Am. Chem. Soc., 1954, 76, 4281.
3. Dictionary of Organometallic Compounds, Chapman and Hall, London, 2nd edn., 1995.
4. P. C. Wailes, R. S. P. Coutts and H. Weigold, Organometallic Chemistry of Titanium, Zirconium, and Hafnium, Academic Press, New York, 1974, p. 302.
5. W. Kaminsky, H. J. Vollmer, E. Heins and H. Sinn, Makromol. Chem., 1974, 175, 443.
6. (a) D. W. Hart and J. Schwartz, J. Am. Chem. Soc., 1974, 96, 8115;
7. (b) D. W. Hart, T. F. Blackburn and J. Schwartz, J. Am. Chem. Soc., 1975, 97, 679;
8. (c) C. A. Bertelo and J. Schwartz, J. Am. Chem. Soc., 1976, 98, 262;
9. (d) J. Schwartz and J. A. Labinger, Angew. Chem., Int. Ed. Engl., 1976, 15, 333.
10. (a) P. C. Wailes and H. Weigold, J. Organomet. Chem., 1970, 24, 405;
11. (b) P. C. Wailes, H. Weigold and A. P. Bell, J. Organomet. Chem., 1971, 27, 373.
12. For reviews, see: (a) G. H. Posner, Org. React., 1975, 22, 253; (b) B. H. Lipshutz, in Organometallics in Synthesis, ed. M. Schlosser, Wiley-VCH, Weinheim, 2nd edn., 2002, ch. VI, p. 665.
13. For reviews, see: (a) G. H. Posner, Org. React., 1975, 22, 253; (b) B. H. Lipshutz, in Organometallics in Synthesis, ed. M. Schlosser, Wiley-VCH, Weinheim, 2nd edn., 2002, ch. VI, p. 665.
14. K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 1972, 94, 4374.
15. R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144.
16. E. Negishi and S. Baba, J. Chem. Soc., Chem. Commun., 1976, 596.
17. S. Baba and E. Negishi, J. Am. Chem. Soc., 1976, 98, 6729.
18. E. Negishi and D. E. Van Horn, J. Am. Chem. Soc., 1977, 99, 3168.
19. N. Okukado, D. E. Van Horn, W. L. Klima and E. Negishi, Tetrahedron Lett., 1978, 1027.
20. E. Negishi, N. Okukado, A. O. King, D. E. Van Horn and B. I. Spiegel, J. Am. Chem. Soc., 1978, 100, 2254.
21. (a) C. A. Bertelo and J. Schwartz, J. Am. Chem. Soc., 1975, 97, 228;
22. (b) J. A. Labinger, D. W. Hart, W. E. Seibert III and J. Schwartz, J. Am. Chem. Soc., 1974, 96, 8115.
23. D. B. Carr and J. Schwartz, J. Am. Chem. Soc., 1979, 101, 3521.
24. For an extensive discussion, see: E. Negishi, in Organometallics in Synthesis, ed. M. Schlosser, Wiley-VCH, Weinheim, 2nd edn., 2002, ch. VIII, p. 925.
25. E. Negishi, Pure Appl. Chem., 1981, 53, 2333.
26. M. Yoshifuji, M. J. Loots and J. Schwartz, Tetrahedron Lett., 1977, 1303.
27. For a review of Pd-catalyzed cross-coupling developed before the advent of the Suzuki and Stille coupling reactions, see: (a) E. Negishi, J. Organomet. Chem., 2002, 653, 34; (b) E. Negishi, in Aspects of Mechanism and Organometallic Chemistry, ed. J. H. Brewster, Plenum, New York, 1978, p. 285; (c) E. Negishi, Acc. Chem. Res., 1982, 15, 340; (d) E. Negishi and F. Liu, in Metal-Catalyzed Cross Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 1.
28. For a review of Pd-catalyzed cross-coupling developed before the advent of the Suzuki and Stille coupling reactions, see: (a) E. Negishi, J. Organomet. Chem., 2002, 653, 34; (b) E. Negishi, in Aspects of Mechanism and Organometallic Chemistry, ed. J. H. Brewster, Plenum, New York, 1978, p. 285; (c) E. Negishi, Acc. Chem. Res., 1982, 15, 340; (d) E. Negishi and F. Liu, in Metal-Catalyzed Cross Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 1.
29. For a review of Pd-catalyzed cross-coupling developed before the advent of the Suzuki and Stille coupling reactions, see: (a) E. Negishi, J. Organomet. Chem., 2002, 653, 34; (b) E. Negishi, in Aspects of Mechanism and Organometallic Chemistry, ed. J. H. Brewster, Plenum, New York, 1978, p. 285; (c) E. Negishi, Acc. Chem. Res., 1982, 15, 340; (d) E. Negishi and F. Liu, in Metal-Catalyzed Cross Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 1.
30. For a review of Pd-catalyzed cross-coupling developed before the advent of the Suzuki and Stille coupling reactions, see: (a) E. Negishi, J. Organomet. Chem., 2002, 653, 34; (b) E. Negishi, in Aspects of Mechanism and Organometallic Chemistry, ed. J. H. Brewster, Plenum, New York, 1978, p. 285; (c) E. Negishi, Acc. Chem. Res., 1982, 15, 340; (d) E. Negishi and F. Liu, in Metal-Catalyzed Cross Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 1.
31. E. Negishi, T. Takahashi, S. Baba, D. E. Van Horn, N. Okukado and F. T. Luo, J. Am. Chem. Soc., 1987, 109, 2393.
32. H. Matsushita and E. Negishi, J. Am. Chem. Soc., 1981, 103, 2882.
33. (a) J. S. Panek and T. Hu, J. Org. Chem., 1997, 62, 4914;
34. (b) T. Ho and J. S. Panek, J. Org. Chem., 1999, 64, 3000.
35. K. E. Drouet and E. A. Theodorakis, J. Am. Chem. Soc., 1999, 121, 456.
36. C. Xu and E. Negishi, Tetrahedron Lett., 1999, 40, 431.
37. E. Negishi, A. Alimardanov and C. Xu, Org. Lett., 2001, 3, 65.
38. F. Zeng and E. Negishi, Org. Lett., 2002, 4, 703.
39. D. E. Van Horn and E. Negishi, J. Am. Chem. Soc., 1978, 100, 2252.
40. (a) J. F. Normant and M. Bourgain, Tetrahedron Lett., 1971, 2583;
41. (b) J. F. Normant and A. Alexakis, Synthesis, 1981, 841.
42. (a) M. J. S. Dewar, Bull. Soc. Chim. Fr., 1951, 18, C71;
43. (b) J. Chatt and L. A. Ducanson, J. Chem. Soc., 1953, 2939.
44. For an earlier review, see: J. Boor, Ziegler-Natta Catalysts and Polymerization, Academic Press, New York, 1978, pp. 670.
45. D. E. Van Horn, L. F. Valente, M. J. Idacavage and E. Negishi, J. Organomet. Chem., 1978, 156, C20.
46. F. N. Tebbe and R. L. Harlow, J. Am. Chem. Soc., 1980, 102, 6149.
47. E. Negishi, D. Y. Kondakov and D. E. Van Horn, Organometallics, 1997, 16, 951.
48. E. Negishi and Z. Tan, Top. Organomet. Chem., 2004, 8, 139.
49. F. Zeng and E. Negishi, Org. Lett., 2001, 3, 719.
50. E. Negishi, S. Liou, C. Xu and S. Huo, Org. Lett., 2002, 4, 261.
51. E. Negishi and T. Yoshida, J. Am. Chem. Soc., 1981, 103, 4985.
52. E. Negishi, D. E. Van Horn and T. Yoshida, J. Am. Chem. Soc., 1985, 107, 6639.
53. R. M. Roberts and A. A. Khalaf, Friedel-Crafts Alkylation Chemistry, Marcel-Dekker, New York, 1984.
54. C. Janiak, in Metallocenes, ed. A. Togni and R. L. Halterman, Wiley-VCH, Weinheim, 1998.
55. (a) E. Negishi, Chem. Eur. J., 1999, 5, 411;
56. (b) See also: E. Negishi and D. Y. Kondakov, Chem. Soc. Rev., 1996, 26, 417.
57. G. A. Olah, Angew. Chem., Int. Ed., 1993, 32, 767.
58. T. Yoshida and E. Negishi, J. Am. Chem. Soc., 1981, 103, 1276.
59. R. F. Jordan, C. S. Bajgur, R. Willett and B. Scott, J. Am. Chem. Soc., 1986, 108, 7410.
60. S. Yamanoi, H. Ohrui, K. Seki, T. Matsumoto and K. Suzuki, Tetrahedron Lett., 1999, 40, 8407.
61. E. Negishi, D. Y. Kondakov, D. Choueiry, K. Kasai and T. Takahashi, J. Am. Chem. Soc., 1996, 118, 9577.
62. (a) H. Sinn and G. Oppermann, Angew. Chem., Int. Ed., 1966, 5, 962;
63. (b) H. Sinn and E. Kolk, J. Organomet. Chem., 1966, 6, 373.
64. (a) W. Kaminsky and H. Sinn, Liebigs Ann. Chem., 1975, 424;
65. (b) W. Kaminsky and H. J. Vollmer, Liebigs Ann. Chem., 1975, 438;
66. (c) W. Kaminsky, J. Kopf, H. Sinn and H. J. Vollmer, Angew. Chem., Int. Ed. Engl., 1976, 15, 629.
67. (a) F. N. Tebbe, G. W. Parshall and G. S. Reddy, J. Am. Chem. Soc., 1978, 100, 3611;
68. (b) K. C. Ott, E. J. M. deBoer and R. H. Grubbs, Organometallics, 1984, 3, 223.
69. J. A. Miller and E. Negishi, Tetrahedron Lett., 1984, 25, 5863.
70. E. Negishi, D. E. Van Horn, T. Yoshida and C. L. Rand, Organometallics, 1983, 2, 563.
71. V. M. Dzhemilev, O. S. Vostrikova and R. M. Sultanov, Izv. Akad. Nauk, SSSR, Ser. Khim., 1983, 218.
72. D. Y. Kondakov and E. Negishi, J. Am. Chem. Soc., 1995, 117, 10771.
73. D. Y. Kondakov and E. Negishi, J. Am. Chem. Soc., 1996, 118, 1577.
74. G. Erker, M. Aulback, M. Knickmeier, D. Wingbermühle, C. Krüger, M. Nolte and S. Werner, J. Am. Chem. Soc., 1993, 115, 4590.
75. E. Negishi, Z. Tan, B. Liang and T. Novak, Proc. Nat. Acad. Sci. USA, 2004, 101, 5782.
76. H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S. Inoue, I. Kasahara and R. Noyori, J. Am. Chem. Soc., 1987, 109, 1596.
77. (a) T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974;
78. (b) See also: T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1.
79. J. P. Morken, M. T. Didiuk and A. H. Hoveyda, J. Am. Chem. Soc., 1993, 115, 6997.
80. M. T. Didiuk, C. W. Johannes, J. P. Morken and A. H. Hoveyda, J. Am. Chem. Soc., 1995, 117, 2943.
81. L. Bell, R. J. Whitby, R. V. H. Jones and M. C. H. Standen, Tetrahedron Lett., 1996, 37, 7139.
82. Y. Yamanaka, M. Hyakutake and M. Mori, J. Am. Chem. Soc., 1997, 119, 7615.
83. R. H. Grubbs and G. W. Coates, Acc. Chem. Res., 1996, 29, 85.
84. S. Huo and E. Negishi, Org. Lett., 2001, 3, 3253.
85. S. Huo, J. Shi and E. Negishi, Angew. Chem., Int. Ed., 2002, 41, 2141.
86. Total Synthesis of Natural Products - The 'Chiron' Approach, ed. S. Hanessian, Pergamon Press, Oxford, UK, 1983.
87. X. Zeng, F. Zeng and E. Negishi, Org. Lett., 2004, 6, 3245.
88. M. Magnin-Lachaux, Z. Tan, B. Liang and E. Negishi, Org. Lett., 2004, 6, 1425.
89. Z. Tan and E. Negishi, Angew. Chem., Int. Ed., 2004, 43, 2911.
90. P. Wipf and S. Ribe, Org. Lett., 2000, 2, 1713.
91. (a) F. H. Köhler, J. Organomet. Chem., 1976, 110, 235;
92. (b) F. H. Köhler, Organomet. Synth., 1988, 4, 52 and references therein.
93. S. Thanedar and M. F. Farona, J. Organomet. Chem., 1982, 235, 65.
94. E. Negishi, F. E. Cederbaum and T. Takahashi, Tetrahedron Lett., 1986, 27, 2829.
95. (a) E. Negishi, S. J. Holmes, J. M. Tour and J. A. Miller, J. Am. Chem. Soc., 1985, 107, 2568;
96. (b) E. Negishi, D. R. Swanson, F. E. Cederbaum and T. Takahashi, Tetrahedron Lett., 1987, 28, 917.
97. E. Negishi, S. J. Holmes, J. M. Tour, J. A. Miller, F. E. Cederbaum, D. R. Swanson and T. Takahashi, J. Am. Chem. Soc., 1989, 111, 3336.
98. For a review, see: E. Negishi, in Comprehensive Organic Synthesis, ed. L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, p. 1163.
99. C. J. Rousset, D. R. Swanson, F. Lamaty and E. Negishi, Tetrahedron Lett., 1989, 30, 5105.
100. P. A. Wender and F. E. McDonald, J. Am. Chem. Soc., 1990, 112, 4956.
101. G. Agnel and E. Negishi, J. Am. Chem. Soc., 1991, 113, 7424.
102. G. Agnel, Z. Owczarczyk and E. Negishi, Tetrahedron Lett., 1992, 33, 1543.
103. (a) M. Mori, N. Uesaka and M. Shibasaki, J. Org. Chem., 1992, 57, 3519;
104. (b) F. Saitoh, M. Mori, K. Okamura and T. Date, Tetrahedron, 1995, 51, 4439.
105. E. Negishi, S. Ma, T. Sugihara and Y. Noda, J. Org. Chem., 1997, 62, 1922.
106. (a) N. Suzuki, M. Nishiura and Y. Wakatsuki, Science, 2002, 295, 660;
107. (b) N. Suzuki, N. Aihara, H. Takahara, T. Watanabe, M. Iwasaki, M. Saburi, D. Hashizume and T. Chihara, J. Am. Chem. Soc., 2004, 126, 60.
108. D. B. Millward and R. M. Waymouth, Organometallics, 1997, 16, 1153.
109. T. Takahashi, Z. Xi, R. Fischer, S. Huo, C. Xi and K. Nakajima, J. Am. Chem. Soc., 1997, 119, 4561.
110. (a) T. Takahashi, N. Suzuki, M. Kageyama, D. Y. Kondakov and R. Hara, Tetrahedron Lett., 1993, 34, 4811;
111. (b) T. Takahashi, D. Y. Kondakov and N. Suzuki, Organometallics, 1994, 13, 3411;
112. (c) N. Suzuki, D. Y. Kondakov, M. Kageyama, M. Kotora, R. Hara and T. Takahashi, Tetrahedron, 1995, 51, 4519.
113. (a) M. Makabe, Y. Sato and M. Mori, Synthesis, 2004, 1369;
114. (b) M. Makabe, Y. Sato and M. Mori, J. Org. Chem., 2004, 69, 6238.
115. (a) H. Ito, K. Omodera, Y. Takigawa and T. Taguchi, Org. Lett., 2002, 4, 1499;
116. (b) Y. Takigawa, H. Ito, K. Omodera and T. Taguchi, Tetrahedron, 2004, 60, 1385.
117. (a) S. S. H. Mao and T. D. Tilley, J. Am. Chem. Soc., 1995, 117, 5365-7031;
118. (b) S. S. Mao, F. Q. Liu and T. D. Tilley, J. Am. Chem. Soc., 1998, 120, 1193;
119. (c) F. Q. Liu, G. Harder and T. D. Tilley, J. Am. Chem. Soc., 1988, 120, 3271;
120. (d) B. L. Lucht, S. S. H. Mao and T. D. Tilley, J. Am. Chem. Soc., 1998, 120, 4354;
121. (e) J. R. Nitschke, S. Zürcher and T. D. Tilley, J. Am. Chem. Soc., 2000, 122, 10345;
122. (f) J. R. Nitschke and T. D. Tilley, Angew. Chem., Int. Ed., 2001, 40, 2142;
123. (g) L. L. Schaefer, J. R. Nitschke, S. S. H. Mao, F.-Q. Liu, G. Harder, M. Haufe and T. D. Tilley, Chem. Eur. J., 2002, 8, 74;
124. (h) S. A. Johnson, F.-Q. Liu, M. C. Suh, S. Zürcher, M. Haufe, S. S. H. Mao and T. D. Tilley, J. Am. Chem. Soc., 2003, 125, 4199.
125. (a) H. G. Alt and M. D. Rausch, J. Am. Chem. Soc., 1974, 96, 5936;
126. (b) D. J. Sikora, M. D. Rausch, R. D. Rogers and J. L. Atwood, J. Am. Chem. Soc., 1979, 101, 5079.
127. (a) K. I. Gell and J. Schwartz, J. Chem. Soc., Chem. Commun., 1979, 244;
128. (b) K. I. Gell, T. V. Harris and J. Schwartz, Inorg. Chem., 1981, 10, 481.
129. (a) G. Erker and K. Dropp, J. Am. Chem. Soc., 1979, 101, 3659;
130. (b) G. Erker, J. Wicher, K. Engel and C. Kriiger, Chem. Ber., 1982, 115, 3300;
131. (c) K. Kropp and G. Erker, Organometallics, 1982, 1, 1246.
132. (a) H. Yasuda, Y. Kajihara, K. Mashima, K. Lee and A. Nakamura, Chem. Lett., 1981, 519;
133. (b) For a review, see:H. Yasuda, K. Tatsumi and A. Nakamura, Acc. Chem. Res., 1985, 18, 120.
134. C. McDade and J. E. Bercaw, J. Organomet. Chem., 1985, 279, 281.
135. (a) S. L. Buchwald, B. T. Watson and J. C. Huffman, J. Am. Chem Soc., 1986, 108, 7411;
136. (b) S. L. Buchwald, R. T. Lum and J. C. Dewan, J. Am. Chem. Soc., 1986, 108, 7441;
137. (c) For a review, see: S. L. Buchwald and R. B. Nielsen, Chem. Rev., 1988, 88, 1047.
138. (a) W. A. Nugent, D. L. Thorn and R. L. Harlow, A. Am. Chem. Soc., 1987, 109, 2788;
139. (b) T. V. RajanBabu, W. A. Nugent, D. F. Taber and P. J. Fagan, J. Am. Chem. Soc., 1988, 110, 7128.
140. I. V. Khand, G. R. Knox, P. L. Pauson, W. E. Watts and M. I. Foreman, J. Chem. Soc., Perkin Trans. 1, 1973, 977.
141. I. Ojima, M. Tzamarioudaki, Z. Li and R. J. Donovan, Chem. Rev., 1996, 96, 635 and references therein.
142. T. T. Takahashi, D. R. Swanson and E. Negishi, Chem. Lett., 1987, 623.
143. T. Takahashi, M. Murakami, M. Kunishige, M. Saburi, Y. Uchida, K. Kozawa, T. Uchida, D. Swanson and E. Negeshi, Chem. Lett., 1989, 761.
144. T. Takahashi, M. Tamura, M. Saburi, Y. Uchida and E. Negishi, J. Chem. Soc., Chem. Commun., 1989, 852.
145. H. G. Alt, C. E. Denner, U. Thewalt and M. D. Rausch, J. Organomet. Chem., 1988, 356, 683.
146. P. Binger, P. Müller, R. Benn, A. Rufinska, B. Gabor, C. Krüger and P. Betz, Chem. Ber., 1989, 122, 1035.
147. K. I. Gell, T. V. Harris and J. Schwartz, Inorg. Chem., 1981, 20, 481.
148. E. Negishi, D. R. Swanson and T. Takahashi, J. Chem. Soc., Chem. Commun., 1990, 1254.
149. T. Takahashi, M. Kageyama, V. Denisov, R. Hara and E. Negishi, Tetrahedron Lett., 1993, 34, 687.
150. J. P. Maye and E. Negishi, Tetrahedron Lett., 1993, 34, 3359.
151. E. Negishi, J. P. Maye and D. Choueiry, Tetrahedron, 1995, 51, 4447.
152. T. Takahashi, C. Xi, Z. Xi, M. Kageyama, R. Fischer, K. Nakajima and E. Negishi, J. Org. Chem., 1998, 63, 6802.
153. E. Negishi, T. Nguyen, J. P. Maye, D. Choueiry, N. Suzuki and T. Takahashi, Chem. Lett., 1992, 2367.
154. (a) E. Negishi and T. Takahashi, Acc. Chem. Res., 1994, 27, 124;
155. (b) E. Negishi and T. Takahashi, Bull. Chem. Soc. Jpn., 1998, 71, 755.
156. E. Negishi and S. Huo, in Titanium and Zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, Weinheim, 2002, eh. 1, pp. 1-49.
157. D. R. Swanson, C. J. Rousset, E. Negishi, T. Takahashi, T. Seki, M. Saburi and Y. Uchida, J. Org. Chem., 1989, 54, 3521.
158. E. Negishi and S. R. Miller, J. Org. Chem., 1989, 54, 6014.
159. (a) U. Rosenthal, A. Ohff, M. Michalek, H. Görls, V. V. Burlekov and V. B. Shur, Angew. Chem., Int. Ed. Engl., 1993, 32, 1193;
160. (b) A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burlakov and V. Rosenthal, Synlett, 1996, 111.
161. (a) T. Takahashi, M. Kotora and M. Kasai, J. Chem. Soc., Chem. Commun., 1994, 2693;
162. (b) Z. Xi, G. Gao, M. Kotora and T. Takahashi, J. Organomet. Chem., 2002, 663, 13.
163. K. Takagi, C. J. Rousset and E. Negishi, J. Am. Chem. Soc., 1991, 113, 1440.
164. T. Takahashi, T. Fujimori, T. Seki, M. Saburi, Y. Uchida, C. J. Rousset and E. Negishi, J. Chem. Soc., Chem. Commun., 1990, 182.
165. K. Fujita, H. Yorimitsu, H. Shinokubo and K. Oshima, J. Org. Chem., 2004, 69, 3302.
166. (a) K. Fujita, H. Shinokubo and K. Oshima, Angew. Chem., Int. Ed., 2003, 42, 2550;
167. (b) K. Fujita, H. Yorimitsu, H. Shinokubo and K. Oshima, J. Am. Chem. Soc., 2004, 126, 6776.
168. (a) H. Ito, T. Taguchi and Y. Hanzawa, Tetrahedron Lett., 1992, 33, 1295;
169. (b) H. Ito, T. Nakamura, T. Taguchi and Y. Hanzawa, Tetrahedron Lett., 1992, 33, 3769;
170. (c) H. Ito, Y. Ikeuchi, T. Taguchi and Y. Hanzawa, J. Am. Chem. Soc., 1994, 116, 5469;
171. (d) H. Ito, T. Nakamura, T. Taguchi and Y. Hanzawa, Tetrahedron, 1995, 51, 4507;
172. (e) H. Ito and T. Taguchi, Tetrahedron Lett., 1997, 38, 5829;
173. (f) Y. Hanzawa, H. Kiyono, N. Tanaka and T. Taguchi, Tetrahedron Lett., 1997, 38, 4615;
174. (g) S. Harada, H. Kiyono, R. Nishio, T. Taguchi and Y. Hanzawa, J. Org. Chem., 1997, 62, 3994;
175. (h) H. Ito, K. Omodera, Y. Takigawa and T. Taguchi, Org. Lett., 2002, 4, 1499.
176. (a) L. A. Paquette and N. Cuniere, Org. Lett., 2002, 4, 1927;
177. (b) L. A. Paquette, R. M. Arbit, J.-A. Funel and S. Bolshakov, Synthesis, 2002, 2105;
178. (c) L. A. Paquette, I. H. Kim and N. Cuniere, Org. Lett., 2003, 5, 221;
179. (d) L. A. Paquette and H.-J. Kang, Tetrahedron, 2004, 60, 1353.
180. (a) P. Bertus, F. Cherouvrier and J. Szymoniak, Tetrahedron Lett., 2001, 42, 1677;
181. (b) P. Bertus, L. Drouin, C. Laroche and J. Szymoniak, Tetrahedron, 2004, 60, 1375.
182. K. Fujita, H. Yorimitsu and K. Oshima, Synlett, 2002, 337.
183. T. Takahashi, M. Kotora, R. Fischer, Y. Nishihara and K. Nakajima, J. Am. Chem. Soc., 1995, 117, 11039.
184. (a) A. Liard and I. Marek, J. Org. Chem., 2000, 65, 7218;
185. (b) S. Farhat and I. Marek, Angew. Chem., Int. Ed., 2002, 41, 1410.
186. J. Li, S. Jeong, L. Esser and P. G. Harran, Angew. Chem., Int. Ed., 2001, 40, 4765.
187. J. Barluenga, L. Álvarez-Rodrizo, F. Rodrignez and F. J. Fañanás, Angew. Chem., Int. Ed., 2004, 43, 3932.
188. E. Negishi, D. Choueiry, T. B. Nguyen, D. R. Swanson, N. Suzuki and T. Takahashi, J. Am. Chem. Soc., 1994, 116, 9751.
189. T. Takaheshi, K. Kasai, N. Suzuki, K. Nakajima and E. Negishi, Organometallics, 1994, 13, 3413.
190. Z. Xi, R. Fischer, R. Hara, W.-H. Sun, Y. Obora, N. Suzuki, K. Nakajima and T. Takaheshi, J. Am. Chem. Soc., 1997, 119, 12842.
191. L. Dupuis, N. Pirio, P. Meunier, A. Igau, B. Donnadieu and J. P. Majoral, Angew. Chem., Int. Ed. Engl., 1997, 36, 987.
192. T. Takahashi, T. Seki, Y. Nitto, M. Saburi, C. J. Rousset and E. Negishi, J. Am. Chem. Soc., 1991, 113, 6266.
193. A. H. Hoveyda and Z. Xu, J. Am. Chem. Soc., 1991, 113, 5079.
194. K. S. Knight and R. M. Waymouth, J. Am. Chem. Soc., 1991, 113, 6268.
195. D. P. Lewis, D. M. Muller, R. J. Whitby and R. V. H. Jones, Tetrahedron Lett., 1991, 32, 6797.
196. T. Takahashi, M. Hasegawa, N. Suzuki, M. Saburi, C. J. Rousset, P. E. Fanwick and E. Negishi, J. Am. Chem. Soc., 1991, 113, 1965.
197. C. J. Rousset, E. Negishi, N. Suzuki and T. Takahashi, Tetrahedron Lett., 1992, 33, 1965.
198. N. Suzuki, D. Y. Kondakov and T. Takahashi, J. Am. Chem. Soc., 1993, 115, 8485.
199. T. Takahashi, K. Aoyagi, V. Denisov, N. Suzuki, D. Choueiry and E. Negishi, Tetrahedron Lett., 1993, 34, 8301.
200. T. Takahashi, M. Kotora and K. Kasai, J. Chem. Soc., Chem. Commun., 1994, 2693.
201. T. Takahashi, D. Y. Kondakov and N. Suzuki, Chem. Lett., 1994, 259.
202. R. Hara, W.-H. Sun, Y. Nishihara and T. Takahashi, Chem Lett., 1997, 1251.
203. E. Negishi, C. J. Rousset, D. Choueiry, J. P. Maye, N. Suzuki and Takahashi, Inorg. Chim. Acta, 1998, 280, 8.
204. S. Gagneur, J. L. Montchamp and E. Negishi, Organometallics, 2000, 19, 2417.
205. P. C. Wailes, H. Weigold and A. P. Bell, J. Organomet. Chem., 1972, 43, C32.
206. D. Röttger and G. Erker, Angew. Chem., Int. Ed. Engl., 1997, 36, 812 and references therein.
207. F. M. G. de Rege, W. M. Davis and S. L. Buchwald, Organometallics, 1995, 14, 4799.
208. (a) J. Terao, T. Watanabe, K. Saito, N. Kambe and N. Sonoda, Tetrahedron Lett., 1998, 39, 9201;
209. (b) J. Terao, Y. Jin, K. Torii and N. Kambe, Tetrahedron, 2004, 60, 1301.
210. T. Takeda, in Titanium and Zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, Weinheim, 2002, ch. 14, pp. 475-500.
211. K. Suzuki, L. Hintermann and S. Yamanoi, in Titanium and Zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, Weinheim, 2002, ch. 8, pp. 282-318.
212. K. Suzuki, T. Hasegawa, T. Imai, H. Maeta and S. Ohba, Tetrahedron, 1995, 51, 4483.
213. Y. Miguel, A. Igau, B. Donnadieu, J. P. Majoral, N. Pirio and P. Meumier, J. Am. Chem. Soc., 1998, 120, 3504.
214. V. Cadierno, A. Igau, B. Donnadieu, A. M. Caminade and J. P. Majoral, Organometallics, 1999, 18, 1580.
215. V. Cadierno, M. Zablocka, B. Donnadieu, A. Igau and J. P. Majoral, Organometellics, 1999, 18, 1882.
216. Y. Miguel, A. Igau, B. Donnadieu, J. P. Majoral, L. Dupuis, N. Pirio and P. Meunier, Chem. Commun., 1997, 279.
217. D. Y. Kondakov and E. Negishi, J. Chem. Soc., Chem. Commun., 1996, 963.
218. N. Etkin, A. J. Hoskin and D. W. Stephan, J. Am. Chem. Soc., 1997, 119, 11420.
219. (a) J. M. Manriquez, D. R. McAlister, R. D. Sanner and J. E. Bercaw, J. Am. Chem. Soc., 1976, 98, 6733;
220. (b) J. M. Manriquez, D. R. McAlister, R. D. Sanner and J. E. Bercaw, J. Am. Chem. Soc., 1978, 100, 2716.
221. G. Erker and F. Rosenfeldt, J. Organomet. Chem., 1980, 188, C1.
222. G. Erker and K. Kropp, J. Organomet. Chem., 1980, 194, 45. For a review, see:; G. Erker, Acc. Chem. Res., 1984, 17, 103.
223. G. Erker and K. Kropp, J. Organomet. Chem., 1980, 194, 45. For a review, see:; G. Erker, Acc. Chem. Res., 1984, 17, 103.
224. E. Negishi, D. R. Swanson and S. R. Miller, Tetrahedron Lett., 1988, 29, 1631.
225. Y. Dumond and E. Negishi, J. Am. Chem. Soc., 1999, 121, 11223.
226. Y. R. Dumond and E. Negishi, Tetrahedron, 2004, 60, 1345.
227. (a) D. A. Straus and R. H. Grubbs, J. Am. Chem. Soc., 1982, 104, 5499;
228. (b) R. M. Waymouth, B. D. Santarsiero, R. J. Coots, M. J. Bronikowski and R. H. Grubbs, J. Am. Chem. Soc., 1986, 108, 1427;
229. (c) R. M. Waymouth, K. R. Clauser and R. H. Grubbs, J. Am. Chem. Soc., 1986, 108, 6385.
230. Y. Hanzawa, in Titanium and zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, Weinheim, 2003, ch. 5, pp. 149-179 and references therein.
231. E. A. Mintz, A. S. Ward and D. S. Tice, Organometellics, 1985, 4, 1308.
232. E. Negishi, K. Akiyoshi, B. O'Connor, K. Takagi and G. Wu, J. Am. Chem. Soc., 1989, 111, 3089.
233. S. Dixon and R. J. Whitby, in Titanium and Zirconium in Organic Synthesis, ed. I. Marek, Wiley-VCH, 2002, ch. 3, pp. 86-109 and references therein.
234. T. Azemi, M. Kitamura and K. Narasaka, Tetrahedron, 2004, 60, 1339.
235. E. Negishi and T. Takahashi in Hauben-Weyl: Science of Synthesis, ed. T. Imamoto, Thieme, Stuttgart, 2002, vol. 2., ch. 2.11, pp. 681-848.