Palladium or platinum complex catalysed reactions of carbonyl and imine compounds with disilanes

Dalton Transactions

Volumn , Issue 2, 2003, Pages 236-243

  Williams, Neil A ^a   Uchimaru, Yuko ^b   Tanaka, Masato ^b,c  

^a KINGSTON UNIVERSITY   (United Kingdom)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL BONDS; COMPLEXATION; PALLADIUM COMPOUNDS; PLATINUM COMPOUNDS; REACTION KINETICS; SILANES;

BENZALDEHYDES; BENZYLIDENEAMINES; CATALYZED REACTIONS; SILYLATION;

CATALYSIS;

EID: 0142016384     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b207987a     Document Type: Article

References (120)

1. Z. Rappoport and Y. Apeloig, Chemistry of Organosilicon Compounds, John Wiley and Sons, New York, 2001, vol. 3;
2. M. A. Brook, Silicon in Organic, Organometallic and Polymer Chemistry, John Wiley and Sons, New York, 2000;
3. U. Schubert, Silicon Chemistry, Springer-Verlag, Vienna, 1999;
4. E. R. Corey, J. Y. Corey and P. P. Gaspar, Silicon Chemistry, Ellis Horwood, Chichester, 1988.
5. R.G. Jones, W. Ando and J. Chojnowski, Silicon-Containing Polymers, Kluwer Academic, Dordrecht, 2000;
6. J. M. Zeigler and F. W. G. Fearon, Silicon-Based Polymer Science, Advances in Chemistry Series 224, American Chemical Society, Washington, DC, 1990.
7. E. P. Pleuddemann, Silane Coupling Agents, Plenum, New York, 1991.
8. J. A. Reichl and D. H. Berry, Adv. Organomet. Chem., 1999, 43, 197;
9. I. Beletskaya and C. Moberg, Chem. Rev., 1999, 99, 3435;
10. K. Horn, Chem. Rev., 1995, 95, 1317;
11. H. K. Sharma and K. H. Pannell, Chem. Rev., 1995, 95, 1351.
12. (a) A. Naka and M. Ishikawa, Organometallics, 2001, 20, 1695;
13. (b) F. Ozawa and J. Kamite, Organometallics, 1998, 17, 5630;
14. (c) Y. Tsuji, R. M. Laso, S. Tomohiro and H. Tsuneishi, Organometallics, 1992, 11, 2353;
15. (d) H. Yamashita, M. Catellani and M. Tanaka, Chem. Lett., 1991, 241;
16. (e) T. Hayashi, A. Kawamoto, T. Kobayashi and M. Tanaka, J. Chem. Soc., Chem. Commun., 1990, 563;
17. (f) T. Hayashi, A. M. Kawamoto, T. Kobayashi, H. Yamashita and M. Tanaka, Organometallics, 1990, 9, 280;
18. (g) T. Hayashi, Y. Matsumoto and Y. Ito, J. Am. Chem. Soc., 1988, 110, 5579;
19. (h) H. Watanabe, M. Saito, M. Sutou, K. Kishimoto, J. Inose and Y. Nagai, J. Chem. Soc., Chem. Commun., 1981, 617;
20. H. Watanabe, M. Kobayashi, M. Saito and Y. Nagai, J. Organomet. Chem., 1981, 216, 149;
21. (j) A. Wada, I. Matsubara, H. Watanabe and Y. Nagai, J. Organomet. Chem., 1980, 199, 185;
22. (k) K. Tamao, S. Okazaki and M. Kumada, J. Organomet. Chem., 1978, 146, 87;
23. K. Tamao, S. Okazaki and M. Kumada, J. Organomet. Chem., 1978, 146, 87;
24. H. Sakurai, Y. Kamiyama and Y. Nakadaira, J. Am. Chem. Soc., 1975, 97, 931;
25. (n) K. Tamao, T. Hayashi and M. Kumada, J. Organomet. Chem., 1976, 114, C19;
26. (o) H. Matsumoto, K. Shono, H. Okinoshima, K. Yamamoto and M. Kumada, J. Am. Chem. Soc., 1972, 94, 9263.
27. H. Yamashita, N. P. Reddy and M. Tanaka, Chem. Lett., 1993, 315.
28. N. P. Reddy, H. Yamashita and M. Tanaka, J. Am. Chem. Soc., 1992, 114, 6596;
29. H. Yamashita, N. P. Reddy and M. Tanaka, Organometallics, 1997, 16, 5223.
30. Y. Ito, T. Matsuura and M. Murakami, J. Am. Chem. Soc., 1988, 110, 3692.
31. Y. Uchimaru, H.-J. Lautenschlager, A. J. Wynd, M. Tanaka and M. Goto, Organometallics, 1992, 11, 263.
32. M. Ishikawa, H. Sakamoto and T. Tabuchi, Organometallics, 1991, 10, 3173;
33. M. Ishikawa, A. Naka, S. Okazaki and H. Sakamoto, Organometallics, 1993, 12, 87;
34. T. Kusukawa, Y. Kabe and W. Ando, Chem. Lett., 1993, 985.
35. A preliminary communication has appeared, see N. A. Williams, Y. Uchimaru and M. Tanaka, J. Chem. Soc., Chem. Commun., 1995, 1129.
36. J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305;
37. H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995;
38. Y. Guari, S. Sabo-Etienne and B. Chaudret, Eur. J. Inorg. Chem., 1999, 1047;
39. G. Dyker, Angew. Chem., Int. Ed., 1999, 38, 1698;
40. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura and Y. Fujiwara, Science, 2000, 287, 1992;
41. C. Jia, W. Lu, T. Kitamura and Y. Fujiwara, Org. Lett., 1999, 1, 2097;
42. K. L. Tan, R. G. Bergman and J. A. Ellman, J. Am. Chem. Soc., 2001, 123, 2685;
43. C. P. Lenses and M. Brookhart, J. Am. Chem. Soc., 1999, 121, 6616;
44. P. W. R. Harris, C. E. F. Rickard and P. D. Woodgate, J. Organomet. Chem., 1999, 589, 168;
45. Y.-G. Lim, J.-B. Kang and Y. H. Kim, J. Chem. Soc., Perkin Trans., 1998, 699;
46. R. Grigg and V. Savic, Tetrahedron Lett., 1997, 38, 5737;
47. G. Halbritter, F. Knoch, A. Wolski and H. Kisch, Angew. Chem., Int. Ed. Engl., 1994, 33, 1603.
48. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda and N. Chatani, Nature, 1993, 366, 529;
49. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda and N. Chatani, Pure Appl. Chem., 1994, 66, 1527;
50. F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani and S. Murai, Bull. Chem. Soc. Jpn., 1995, 68, 62;
51. N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi and S. Murai, J. Am. Chem. Soc., 2001, 123, 10935;
52. F. Kakiuchi, T. Sato, K. Igi, N. Chatani and S. Murai, Chem. Lett., 2001, 422;
53. F. Kakiuchi, T. Sato, K. Igi, N. Chatani and S. Murai, Chem. Lett., 2001, 386;
54. F. Kakiuchi, M. Matsumoto, M. Sonoda, T. Fukuyama, N. Chatani and S. Murai, Chem. Lett., 2000, 750;
55. F. Kakiuchi, T. Sato, M. Yamauchi, N. Chatani and S. Murai, Chem. Lett., 1999, 19;
56. F. Kakiuchi, T. Sato, T. Tsujimoto, M. Yamauchi, N. Chatani and S. Murai, Chem. Lett., 1998, 1053.
57. (a) T. Sakakura, Y. Tokunaga, T. Sodeyama and M. Tanaka, Chem. Lett., 1987, 2375;
58. (b) Y. Uchimaru, A. M. M. El-Sayed and M. Tanaka, Organometallics, 1993, 12, 2065;
59. K. Ezbiansky, P. I. Djurovich, M. LaForest, D. J. Sinning, R. Zayes and D. H. Berry, Organometallics, 1998, 17, 1455.
60. (a) C.-H. Jun, J.-B. Hong, Y.-H. Kim and K.-Y. Chung, Angew. Chem., Int. Ed., 2000, 39, 3440;
61. (b) Y. Ie, N. Chatani, T. Ogo, D. R. Marshall, T. Fukuyama, F. Kakiuchi and S. Murai, J. Org. Chem., 2000, 65, 1475-1488.
62. C. Amatore, A. Jutand, F. Khalil, M. A. M'Barki and L. Mottier, Organometallics, 1993, 12, 3168.
63. D. Seyferth, E. W. Goldman and J. Escudie, J. Organomet. Chem., 1984, 271, 337.
64. H. Yamashita, M. Goto and M. Tanaka, Organometallics, 1997, 16, 4696.
65. M. Suginome, H. Oike, P. H. Schuff and Y. Ito, Bull. Chem. Soc. Jpn., 1996, 69, 289;
66. M. Suginome, H. Oike, P. H. Schuff and Y. Ito, Organometallics, 1996, 15, 2170;
67. M. Murakami, T. Yoshida and Y. Ito, Organometallics, 1994, 13, 2900;
68. H. Yamashita, M. Tanaka and M. Goto, Organometallics, 1992, 11, 3232;
69. Y. Pan, J. T. Mague and M. J. Fink, Organometallics, 1992, 11, 3495;
70. M. Tanaka, Y. Uchimaru and H.-J. Lautenschlager, Organometallics, 1991, 10, 16;
71. H. Yamashita, T.-a. Kobayashi, T. Hayashi and M. Tanaka, Chem. Lett., 1990, 1447;
72. T.-A. Kobayashi, T. Hayashi, H. Yamashita and M. Tanaka, Chem. Lett., 1989, 467.
73. Ozawa and J. Kamite, Organometallics, 1998, 17, 5630;
74. H. Yamashita, M. Tanaka and M. Goto, Organometallics, 1992, 11, 3232.
75. L. Johnson and J. A. Gladysz, Inorg. Chem., 1981, 20, 2508;
76. J. A. Gladysz, Acc. Chem. Res., 1984, 17, 326.
77. (a) K. Hasabe, J. Kamite, T. Mori, H. Katayama and F. Ozawa, Organometallics, 2000, 19, 2022 and the references cited therein;
78. (b) Y. Tanaka, H. Yamashita, S. Shimada and M. Tanaka, Organometallics, 1997, 16, 3246.
79. For homolytic cleavage of benzylic metal species, see D. H. Hill, M. A. Parvez and A. Sen, J. Am. Chem. Soc., 1994, 116, 2889.
80. (a) K. H. Pannell and H. Sharma, Organometallics, 1991, 10, 954;
81. (b) K. Tamao, Y. Tarao, Y. Nakagawa, K. Nagata and Y. Ito, Organometallics, 1993, 12, 1113;
82. H. Yamashita, M. Tanaka and M. Goto, Organometallics, 1992, 11, 3227;
83. Y. Tanaka, H. Yamashita and M. Tanaka, Organometallics, 1995, 14, 530;
84. (e) J. D. Rich, J. Am. Chem. Soc., 1989, 111, 5886.
85. (a) W. Ando, M. Ikeno and A. Sekiguchi, J. Am. Chem. Soc., 1977, 99, 6447;
86. (b) W. Ando, M. Ikeno and A. Sekiguchi, J. Am. Chem. Soc., 1978, 100, 3613.
87. A. Schafer, M. Weidenbruch and S. Pohl, J. Organomet. Chem., 1985, 282, 305.
88. W. Ando, Y. Hamada, A. Sekiguchi and K. Ueno, Tetrahedron Lett., 1982, 23, 5323.
89. B. Gehrhus, P. B. Hitchcock and M. F. Lappert, Organometallics, 1997, 16, 4861.
90. C. M. Anderson, R. J. Puddephatt, G. Ferguson and A. J. Lough, J. Chem. Soc., Chem. Commun., 1989, 1297;
91. C. M. Anderson, M. Crespo, M. C. Jennings, A. J. Lough, G. Ferguson and R. J. Puddephatt, Organometallics, 1991, 10, 2672;
92. M. Crespo, M. Martinez, J. Sales, X. F. Solans and M. Font-Bardia, Organometallics, 1992, 11, 1288;
93. M. Crespo, M. Martinez and J. Sales, J. Chem. Soc., Chem. Commun., 1993, 822;
94. M. Crespo, M. Martinez and J. Sales, Organometallics, 1993, 12, 4297.
95. Sonoda, N. Kakiuchi, N. Chatani and S. Murai, Bull. Chem. Soc. Jpn., 1997, 70, 3117.
96. R. H. Crabtree, Chem. Rev., 1985, 85, 245.
97. S. Sakaki and M. Ieki, J. Am. Chem. Soc., 1993, 115, 2373.
98. Q. Jiang, D. C. Pestana, P. J. Carroll and D. H. Berry, Organometallics, 1994, 13, 3679.
99. W. Chen, S. Shimada and M. Tanaka, Science, 2002, 295, 308;
100. S. Shimada, M. Tanaka and M. L. N. Rao, Organometallics, 1999, 18, 291;
101. S. Shimada, M. Tanaka and K. Honda, J. Am. Chem. Soc., 1995, 117, 8289;
102. S. Shimada, M. Tanaka and M. Shiro, Angew. Chem., Int. Ed. Engl., 1996, 35, 1856.
103. P. Caston, J. Laud, N. P. Johnson and R. Souls, J. Am. Chem. Soc., 1985, 107, 5011.
104. The major product appeared to be α-trimethylsilylstyrene. The details will be reported separately.
105. D. R. Coulson, Inorg. Synth., 1972, 13, 121.
106. J. G. Evans, P. L. Goggin, R. L. Goodfellow and J. G. Smith, J. Chem. Soc. A, 1968, 464.
107. F. G. Mann and D. Puride, J. Chem. Soc., 1935, 1549.
108. A. O. King, E. Negishi, F. J. Villani Jr. and A. Silveira Jr., J. Org. Chem., 1978, 43, 358.
109. T. Hayashi, M. Konishi and M. Kumada, Tetrahedron Lett., 1979, 1871.
110. M. Tanaka, T.-a. Kobayashi and T. Sakakura, Nippon Kagaku Kaishi, 1985, 537.
111. Y. Takahashi, T. Ito, S. Sakai and Y. Ishii, J. Chem. Soc., Chem. Commun., 1970, 1065.
112. K. Moseley and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1974, 169;
113. A. Keasey, B. E. Mann, A. Yates and P. M. Maitlis, J. Organomet. Chem., 1978, 152, 117.
114. R. Ugo, F. Cariati and G. La Monica, Inorg. Synth., 1968, 11, 105.
115. K. A. Jensen, Z. Anorg. Chem., 1936, 229, 225.
116. C. D. Cook and G. S. Jauhal, J. Am. Chem. Soc., 1968, 90, 1467.
117. M. L. H. Green, H. Murakata and T. Saito, J. Chem. Soc. A, 1971, 468.
118. R. A. Schunn, Inorg. Synth., 1974, 15, 5.
119. M. Kumada, M. Yamaguchi, Y. Yamamoto, J. Nakajima and K. Shiina, J. Org. Chem., 1956, 21, 1264.
120. M. Kumada, K. Tamao, T. Takabo and M. Ishikawa, J. Organomet. Chem., 1967, 9, 43.