Insertion chemistry into metal–carbon bonds

Abstract

References

1. E. W. Abel, F. G. A. Stone and G. Wilkinson(Editors), in Comprehensive Organometallic Chemistry II, Pergamon, Oxford, 1995.
2. F. A. Cotton, Chem. Rev., 1955, 55, 551.
3. K. Ziegler, E. Holtzkamp, H. Breil and H. Martin, Angew. Chem., 1955, 67, 541.
4. G. Fink, R. Mulhaupt and H. H. Brintzinger (Editors), Ziegler Catalysts, Springer, Berlin, Heidelberg, 1995.
5. P. Cossee, J. Catal., 1964, 3, 80.
6. M. Bochmann, J. Chem. Soc., Dalton Trans., 1996, 255.
7. G. Wilke, J. Organomet. Chem., 1980, 200, 349.
8. A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida and A. Misono, J. Am. Chem. Soc., 1965, 87, 4652; T. Saito, Y. Uchida, A. Misono, A. Yamamoto, K. Morifuji and S. Ikeda, J. Am. Chem. Soc., 1965, 88, 5198.
9. A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida and A. Misono, J. Am. Chem. Soc., 1966, 90, 5198.
10. T. Saito, Y. Uchida, A. Misono, A. Yamamoto, K. Morifuji and S. Ikeda, J. Organomet. Chem., 1966, 6, 572.
11. A. Yamamoto and S. Ikeda, J. Am. Chem. Soc., 1967, 89, 5989.
12. T. Yamamoto, A. Yamamoto and S. Ikeda, J. Am. Chem. Soc., 1971, 93, 3350.
13. T. Yamamoto, A. Yamamoto and S. Ikeda, J. Am. Chem. Soc., 1971, 93, 3360.
14. A. S. Abu-Surrah and B. Rieger, Angew. Chem., 1996, 35, 2475.
15. A. Yamamoto, T. Shimizu and S. Ikeda, Makromol. Chem., 1970, 136, 297.
16. A. Yamamoto, T. Shimizu and S. Ikeda, Polymer J., 1970, 1, 171.
17. T. Yamamoto, A. Yamamoto and S. Ikeda, Polymer Lett., 1971, 9, 281.
18. T. Yamamoto, A. Yamamoto and S. Ikeda, Bull. Chem. Soc. Jpn., 1972, 45, 1104.
19. T. Yamamoto, A. Yamamoto and S. Ikeda, Bull. Chem. Soc. Jpn., 1972, 45, 1111.
20. T. Yamamoto, A. Yamamoto and S. Ikeda, Polymer Lett., 1972, 10, 835.
21. See A. Yamamoto, Ann. N. Y. Acad. Sci., 1974, 239, 60; A. Yamamoto and S. Ikeda, in Ionic Polymerization. Unsolved Problems. eds. J. Furukawa and O. Vogel, Marcel Dekker, New York, 1976; A. Yamamoto and S. Ikeda, Prog. Polym. Sci. Jpn., 1972, 3, 49; A. Yamamoto and T. Yamamoto, J. Polym. Sci. Macromol. Rev., 1978, 13.
22. See C. M. Killian, D. J. Tempel, L. K. Johnson and M. Brookhart, J. Am. Chem. Soc., 1996, 118, 11664.
23. A. Sen, Acc. Chem. Res., 1993, 26, 303.
24. G. J. P. Britovsek, V. C. Gibson, B. S. Kimberley, P. J. Maddox, S. J. McTavish, G. A. Solan, A. J. P. White and D. J. Williams, Chem. Commun., 1998, 845.
25. B. L. Small, M. Brookhart and A. M. A. Bennett, J. Am. Chem. Soc., 1998, 120, 4049.
26. M. Uchino, A. Yamamoto and S. Ikeda, J. Organomet. Chem., 1970, 24, C63; M. Uchino, K. Asagi, A. Yamamoto and S. Ikeda, J. Organomet. Chem., 1976, 84, 93.
27. K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 1972, 94, 4374, 9278.
28. K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato and M. Kumada, Bull. Chem. Soc. Jpn., 1976, 49, 1958.
29. R. J. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144.
30. F. Diedrich and P. J. Stang(Editors), Metal-catalyzed Cross-coupling Reactions, Wiley-VCH, Weinheim, 1998 and refs. cited therein.
31. T. Yamamoto and M. Abla, J. Organomet. Chem., 1997, 535, 209.
32. F. Ozawa, M. Fujimori, T. Yamamoto and A. Yamamoto, Organometallics, 1986, 5, 2144.
33. F. Ozawa, T. Ito and A. Yamamoto, J. Am. Chem. Soc., 1980, 102, 6457; F. Ozawa, T. Ito, Y. Nakamura and A. Yamamoto, Bull. Chem. Soc. Jpn., 1981, 54, 1868; S. Komiya, Y. Morimoto, A. Yamamoto and T. Yamamoto, Organometallics, 1982, 1, 1528; S. Komiya, Y. Abe, A. Yamamoto and T. Yamamoto, Organometallics, 1983, 2, 1446; F. Ozawa, K. Kurihara, T. Yamamoto and A. Yamamoto, Bull. Chem. Soc. Jpn., 1985, 58, 399.
34. K. Tatsumi, R. Hoffmann, A. Yamamoto and J. K. Stille, Bull. Chem. Soc. Jpn., 1981, 54, 1857; K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto and T. Yamamoto, J. Am. Chem. Soc., 1984, 106, 8181.
35. A. Yamamoto, T. Yamamoto, S. Komiya and F. Ozawa, Pure Appl. Chem., 1984, 56, 1621.
36. F. Ozawa, K. Kurihara, T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 1985, 279, 233.
37. T. Yamamoto, T. Kohara and A. Yamamoto, Chem. Lett., 1976, 1217; Bull. Chem. Soc. Jpn., 1981, 54, 2161.
38. F. Ozawa and A. Yamamoto, Chem. Lett., 1981, 289.
39. F. Ozawa and A. Yamamoto, Chem. Lett., 1982, 865.
40. F. Ozawa, H. Soyama, T. Yamamoto and A. Yamamoto, Tetrahedron Lett., 1982, 23, 3383.
41. T. Kobayashi and M. Tanaka, J. Organomet. Chem., 1982, 233, C64.
42. For reviews, see ref. 35; A. Yamamoto, F. Ozawa, H. Nakazawa and T. Yamamoto, New Frontiers in Organometallic and Inorganic Chemistry, eds. Y. H. Huang, A. Yamamoto and B. K. Teo, Science Press, Beijing, 1984; A. Yamamoto, T. Yamamoto and F. Ozawa, Pure Appl. Chem., 1985, 57, 1789; A. Yamamoto, F. Ozawa and T. Yamamoto, Fundamental Research in Homogeneous Catalysis, ed. A. E. Shilov, Gordon & Breach Science Publ., London, 1986; A. Yamamoto, F. Ozawa, K. Osakada, L. Huang, T. I. Son, N. Kawasaki and M. K. Doh, Pure Appl. Chem., 1991, 63, 687.
43. F. Ozawa, T. Sugimoto, T. Yamamoto and A. Yamamoto, Organometallics, 1984, 3, 692.
44. See T.-M. Huang, Y.-J. You, C.-S. Yang, W.-H. Tseng, J.-T. Chen, M.-C. Cheng and Yu. Wang, Organometallics, 1991, 10, 1026; J.-T. Chen, Yu.-S. Yeh, G.-H. Lee and Y. Wang, J. Organomet. Chem., 1991, 414, C64; J.-T. Chen, W. H. Tzeng, F. Y. Tsai, M. C. Cheng and Y. Wang, Organometallics, 1991, 10, 3954.
45. Y.-S. Lin and A. Yamamoto, Organometallics, 1998, 17, 3466; Tetrahedron Lett., 1997, 38, 3747; Bull. Chem. Soc. Jpn., 1998, 71, 723.
46. F. Ozawa, N. Kawasaki, T. Yamamoto and A. Yamamoto, Chem. Lett., 1985, 567; M. Tanaka, T. Kobayashi, T. Sakakura, H. Itatani, K. Danno and K. Zushi, J. Mol. Catal., 1985, 32, 115; M. Tanaka, T. Kobayashi and T. Sakakura, J. Chem. Soc., Chem. Commun., 1985, 537; F. Ozawa, N. Kawasaki, H. Okamoto, T. Yamamoto and A. Yamamoto, Organometallics, 1987, 6, 1640.
47. F. Kawataka, Y. Kayaki, I. Shimizu and A. Yamamoto, Organometallics, 1994, 13, 3517.
48. See (a) E. Drent, J. A. M. van Broekhoven and P. H. M. Budzelaar, Recl. Trav. Chim. Pays-Bas, 1996, 115, 263; (b) A. Sen, Acc. Chem. Res., 1993, 303; (c) M. Sperre and G. Consiglio, Chem. Ber./Recueil, 1997, 130, 1557.
49. F. C. Rix, M. Brookhart and P. S. White, J. Am. Chem. Soc., 1996, 118, 4746.
50. See J. H. Green, J. G. P. Delis, P. W. N. M. van Leeuwen and K. Vrieze, Organometallics, 1997, 16, 68.
51. For example, see D. G. Musaev, R. D. J. Froose, M. Svenson and K. Morokuma, J. Am. Chem. Soc., 1997, 119, 367; L. Deng, M. Margl and T. Ziegler, J. Am. Chem. Soc., 1997, 119, 1094.
52. A. Yamamoto, J. Organomet. Chem., 1995, 500, 337.
53. A. Yamamoto and Y. Kayaki, Synlett., to be submitted.
54. F. Kawataka, I. Shimizu and A. Yamamoto, Bull. Chem. Soc. Jpn., 1995, 68, 654.
55. Y. Kayaki, I. Shimizu and A. Yamamoto, Chem. Lett., 1995, 1089.
56. Y. Kayaki and A. Yamamoto, J. Synth. Org. Chem. Jpn. (Japanese), 1998, 56, 96.
57. Y. Kayaki, I. Shimizu and A. Yamamoto, Bull. Chem. Soc. Jpn., 1997, 70, 917.
58. Y. Kayaki, I. Shimizu and A. Yamamoto, Bull. Chem. Soc. Jpn., 1997, 70, 1135.
59. Y. Kayaki, I. Shimizu and A. Yamamoto, Bull. Chem. Soc. Jpn., 1997, 70, 1141.
60. K. Karabelas and A. Hallberg, Tetrahedron Lett., 1985, 26, 3131; K. Karabelas, C. Westerlund and A. Hallberg, J. Org. Chem., 1985, 50, 3896; K. Karabelas and A. Hallberg, J. Org. Chem., 1986, 51, 5286; M. M. Abelman, T. Oh and L. E. Overman, J. Am. Chem. Soc., 1988, 110, 2328 and other recent examples.
61. For example, K. Nozaki, N. Sato, Y. Tonomura, M. Yasutomi, H. Takaya, T. Hiyama, T. Matsubara and N. Koga, J. Am. Chem. Soc., 1997, 119, 12779.
62. F. Ozawa, M. Nakano, I. Aoyama, T. Yamamoto and A. Yamamoto, J. Chem. Soc., Chem. Commun., 1986, 382.
63. H. C. Volger and K. Vrieze, J. Organomet. Chem., 1968, 13, 495; G. Carturan and G. Nardin, J. Organomet. Chem., 1990, 390, 2647.
64. F. Ozawa, T. I. Son, K. Osakada and A. Yamamoto, J. Chem. Soc., Chem. Commun., 1989, 1067.
65. A. Yamamoto, Adv. Organomet. Chem., Vol. 34, 1992, 34, 111.
66. Y.-S. Lin and A. Yamamoto, Topics in Organometallic Chemistry, Activation of Unreactive Bonds and Organic Synthesis, ed. S. Murai, Springer, Heidelberg, 1999, to be published.
67. M. Oshima, I. Shimizu, A. Yamamoto and F. Ozawa, Organometallics, 1991, 10, 1221.
68. A. Yamamoto, Bull. Chem. Soc. Jpn., 1995, 68, 433.
69. T. Terashima, I. Shimizu and A. Yamamoto, unpublished results.
70. M. Sakamoto, I. Shimizu and A. Yamamoto, Bull. Chem. Soc. Jpn., 1996, 69, 1065.
71. F. Ozawa, T. Son, S. Ebina, K. Osakada and A. Yamamoto, Organometallics, 1992, 11, 171.
72. S. Komiya, A. Yamamoto and T. Yamamoto, Chem. Lett., 1981, 115.
73. K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu and A. Yamamoto, Chem. Lett., 1995, 367.
74. M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl and J. G. de Vries, Angew. Chem., Int. Ed. Engl., 1998, 37, 662.
75. K. Nagayama, I. Shimizu and A. Yamamoto, Chem. Lett., 1998, 1143.
76. A. Yamamoto and Y. Kayaki, Synlett, to be submitted.