The first alkyl(silyl)palladium complexes: Formation by oxidative addition of silacyclobutanes to palladium complexes, reductive elimination, and other reactivities relevant to catalysis

Organometallics

Volumn 16, Issue 15, 1997, Pages 3246-3248

  Tanaka, Yoshifumi ^a   Yamashita, Hiroshi ^b   Shimada, Shigeru ^b   Tanaka, Masato ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007867069     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970186j     Document Type: Article

References (37)

1. -1, respectively. See: Gordon, M. S.; Boatz, J. A.; Walsh, R. J. Phys. Chem. 1989, 93, 1584.
2. (a) Weyenberg, D. R.; Nelson, L. E. J. Org. Chem. 1965, 30, 2618.
3. (b) Nametkin, N. S.; Ushakov, N. V.; Vdovin, V. M. Vysokomol. Soedin., Ser. A 1971, 13, 29; Chem. Abstr. 1971, 74, 88325w.
4. (b) Nametkin, N. S.; Ushakov, N. V.; Vdovin, V. M. Vysokomol. Soedin., Ser. A 1971, 13, 29; Chem. Abstr. 1971, 74, 88325w.
5. (c) Cundy, C. S.; Eaborn, C.; Lappert, M. F. J. Organomet. Chem. 1972, 44, 291 and references cited therein.
6. (d) Poletaev, V. A.; Vdovin, V. M.; Nametkin, N. S. Dokl. Akad. Nauk SSSR 1973, 208, 1112; Chem. Abstr. 1973, 79, 19191r.
7. (d) Poletaev, V. A.; Vdovin, V. M.; Nametkin, N. S. Dokl. Akad. Nauk SSSR 1973, 208, 1112; Chem. Abstr. 1973, 79, 19191r.
8. (e) Finkel'shtein, E. Sh.; Ushakov, N. V.; Pritula, N. A.; Andreev, E. A.; Plate, N. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1992, 223; Chem. Abstr. 1992, 116, 256191f.
9. (e) Finkel'shtein, E. Sh.; Ushakov, N. V.; Pritula, N. A.; Andreev, E. A.; Plate, N. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1992, 223; Chem. Abstr. 1992, 116, 256191f.
10. (f) Ushakov, N. V.; Yarysheva, A. Yu.; Tal'roze, R. V.; Finkel'shtein, E. Sh.; Plate, N. A. Dokl. Akad. Nauk 1992, 325, 964; Chem. Abstr. 1993, 118, 102788k.
11. (f) Ushakov, N. V.; Yarysheva, A. Yu.; Tal'roze, R. V.; Finkel'shtein, E. Sh.; Plate, N. A. Dokl. Akad. Nauk 1992, 325, 964; Chem. Abstr. 1993, 118, 102788k.
12. (g) Bialecka-Florjanczyk, E.; Ganicz, T.; Stanczyk, W.; Sledzinska, I. Polimery (Warsaw) 1993, 38, 424; Chem. Abstr. 1994, 121, 36351w.
13. (g) Bialecka-Florjanczyk, E.; Ganicz, T.; Stanczyk, W.; Sledzinska, I. Polimery (Warsaw) 1993, 38, 424; Chem. Abstr. 1994, 121, 36351w.
14. (h) Liao, C. X.; Chen, M. W.; Sun, L.; Weber, W. P. J. Inorg. Organomet. Polym. 1993, 3, 231.
15. Yamashita, H.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8873.
16. Reddy, N. P.; Hayashi, T.; Tanaka, M. Chem. Commun. 1996, 1865.
17. Sakurai, H.; Imai, T. Chem. Lett. 1975, 891. Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461.
18. Sakurai, H.; Imai, T. Chem. Lett. 1975, 891. Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461.
19. Cundy, C. S.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1972, 445.
20. PP = 9.6 Hz).
21. Johnson, C. K. ORTEP, a FORTRAN Thermal-Ellipsoid Plot Program for Crystal Structure Illustrations; Report ORNL-3794; Oak Ridge National Laboratory: Oak Ridge, TN, 1970.
22. w = 0.075. The non-hydrogen atoms were refined anisotropically. The hydrogen atoms were generated at idealized calculated positions. All hydrogen atoms were then included in the calculations but not refined. All calculations were performed using the Crystan GM crystallographic software package.
23. The high thermal parameters for C(6) suggest that C(6) is disordered.
24. (a) Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495.
25. (b) Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900.
26. (c) Suginome, M.; Oike, H.; Ito, Y. Organometallics 1994, 13, 4148.
27. (d) Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408.
28. (e) Suginome, M.; Oike, H.; Shuff, P. H.; Ito, Y. Organometallics 1996, 15, 2170.
29. (f) Shimada, S.; Tanaka, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1856.
30. Broadwood-Strong, G. T. L.; Chaloner, P. A.; Hitchcock, P. B. Polyhedron 1993, 12, 721.
31. 2 behaved very similarly to give 4a (90% based on Pd) when treated with 1a at 60°C for 30 min.
32. 1H NMR and a black precipitate (presumably metallic palladium).
33. 2P of 3a (0.66-0.95 ppm), the yield of (PhC≡CPh)-Pd(dmpe) was readily evaluated by integration.
34. Ozawa, F.; Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844.
35. 11 reductive elimination from a T-shaped intermediate generated via dissociation of one of the phosphorus atoms of the dmpe ligand is also plausible. Such a mechanism is more generally accepted for the reductive elimination from cis-dialkylpalladium species. See: Yamamoto, A. Organotransition Metal Chemistry: Fundamental Concepts and Applications; Wiley-Interscience: New York, 1986; p 240.
36. (b) Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; Wiley-Interscience: New York, 1988; p 151.
37. Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3350.