Synthesis of (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes and the related ethenes, precursors to stereodefined germylethenes, via Pd(dba)2-P(OCH2)3CEt-catalyzed germastannation of acetylenes in THF

Journal of Organometallic Chemistry

Volumn 622, Issue 1-2, 2001, Pages 302-308

  Senda, Yoshiya ^a   Oguchi, Y ^a   Terayama, Michihiro ^a   Asai, Taijyu ^a   Nakano, Taichi ^a   Migita, Toshihiko ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

(Z) Germyl(stannyl)ethenes; Acetylenes; Germastannation; Germylstannane; Palladium catalysis

Indexed keywords

EID: 0042379793     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)00652-0     Document Type: Article

References (44)

1. (a) H. Okinoshima, K. Yamamoto, M. Kumada, J. Organomet. Chem. 86 (1975) C27.
2. (b) H. Sakurai. Y. Kamiyama, Y. Nakadaira, J. Am. Chem. Soc. 97 (1975) 931.
3. © K. Tamao, T. Hayashi, M. Kumada, J. Organomet. Chem. 114 (1976) C19.
4. (d) H. Watanabe, M. Kobayashi, K. Higuchi, Y. Nagai, J. Organomet. Chem. 186 (1980) 51.
5. (e) Y. Ito, M. Suginome, M. Murakami, J. Org. Chem. 56 (1991) 1948.
6. (f) H. Yamashita, M. Catellani, M. Tanaka, Chem. Lett. (1991) 241.
7. (a) T. Hayashi, H. Yamashita, T. Sakakura, Y. Uchimaru, M.Tanaka, Chem. Lett. (1991) 245.
8. (b) K. Mochida, C. Hodota, H. Yamashita, M. Tanaka, Chem. Lett. (1992) 1635.
9. (a) T.N. Mitchell H. Killing, R. Dicke, R. Wickenkamp, J. Chem. Soc. Chem. Commun. (1985) 354.
10. (b) B.L. Chenard. E.D. Laganis, F. Davidson, T.V. RajanBabu, J. Org. Chem. 50 (1985) 3666.
11. © B.L. Chenard, C.M. Van Zyl, J. Org. Chem. 51 (1986) 3561.
12. (d) B.L. Chenard, C.M. Van Zyl, D.R. Sanderson, Tetrahedron Lett. 27 (1986) 2801.
13. (e) T.N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, U. Schneider, J. Org. Chem. 52 (1987) 4868.
14. (f) K. Ritter, Synthesis (1989) 218.
15. (g) M. Mori, N. Watanabe, N. Kaneta, M. Shibasaki, Chem. Lett. (1991) 1615.
16. (h) M. Murakami, H. Amii, N. Takizawa, Y. Ito, Organometallics 12 (1993) 4223.
17. (a) T.N. Mitchell, A. Amamria, H. Killing, D. Rutschow, J. Organomet. Chem. 241 (1983) C45.
18. (b) T.N. Mitchell, A. Amamria, H. Killing, D. Rutschow, J. Organomet. Chem. 304 (1986) 257.
19. © T.N. Mitchell, B. Kowall, J. Organomet. Chem. 437 (1992) 127.
20. (d) E. Piers, R.T. Skerlj, Can. J. Chem. 72 (1994) 2468.
21. (a) M. Kosugi, Y. Shimizu, T. Migita, Chem. Lett. (1977) 1423.
22. (b) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 100 (1978) 3636.
23. © J.K. Stille, Angew. Chem. Int. Ed. Engl. 25 (1986) 508.
24. (a) A. Hallberg, C. Westerlund, Chem. Lett. (1982) 1933.
25. (b) J. Yoshida, K. Tamao, H. Yamamoto, T. Kakui, T. Uchida, M. Kumada, Organometallics 1 (1982) 542.
26. © K. Ikenaga, K. Kikukawa, T. Matsuda, J. Chem. Soc. Perkin Trans. 1 (1986) 1959.
27. (d) H. Hatanaka, T. Hiyama, J. Org. Chem. 53 (1988) 918.
28. (e) Y. Hatanaka, T. Hiyama, J. Org. Chem. 54 (1989) 268.
29. (f) K. Karabelas, A. Hallberg, J. Org. Chem. 54 (1989) 1773.
30. (g) Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 31 (1990) 2719.
31. Lukevics E., Arsenyan P., Veveris M. Metal Based Drugs. 5:1998;251.
32. E. Piers, R.T. Skerlj, J. Chem. Soc. Chem. Commun. (1987) 1025.
33. Mitchell T.N., Schneider U., Fröhling B. J. Organomet. Chem. 384:1990;C53.
34. (a) A. Naka, T. Okada, M. Ishikawa, J. Organomet. Chem. 521 (1996) 163.
35. (b) Ozawa, T. Hikida, Organometallics, 15 (1996) 4501.
36. © H. Yamashita, T. Kobayashi, M. Tanaka, J. A. Samuels, W. E. Streib, Organometallics, 11 (1992) 2330.
37. (a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. (1975) 4467.
38. (b) D.E. Ames, D. Bull, C. Takundwa, Synthesis (1981) 364.
39. © N.A. Bumagin, A.B. Ponomaryov, I.P. Beletskaya, Synthesis (1984) 728.
40. Y. Takahashi, Ts. Ito, S. Sakai, Y. Ishii, J. Chem. Soc. Chem. Commun. (1970) 1065.
41. Osborn J.A., Wilkinson G. Inorg.Synth. 10:1967;67.
42. Hallman P.S., Stephenson T.A., Wilkinson G. Inorg. Synth. 12:1972;238.
43. Jensen K.A. Z. Anorg. Chem. 229:1936;225.
44. Tamborski C., Ford F.E., Soloski E.J. J. Org. Chem. 28:1963;237.