Metal-dependent stabilization of Si-S bonds to hydrolysis in iridium and rhodium silyls. Hydrolyzability as a probe for Si-H reductive elimination

Organometallics

Volumn 15, Issue 3, 1996, Pages 1075-1078

  Aizenberg, Michael ^a   Goikhman, Roman ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037611473     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950791r     Document Type: Article

References (39)

1. (a) Chang, L. S.; Johnson, M. P.; Fink, M. J. Organometallics 1991, 10, 1219.
2. (b) Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Wright, L. J. J. Am. Chem. Soc. 1992, 114, 9682.
3. (c) Malisch, W.; Schmitzer, S.; Kaupp, G.; Hindahl, K.; Käb, H.; Wachtler, U. In Organosilicon Chemistry. From Molecules to Materials; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1994; p 185.
4. Adam, W.; Azzena, U.; Prechtl, F.; Hindahl. K.; Malisch, W. Chem. Ber. 1992, 125, 1409.
5. Goikhman, R.; Aizenberg, M.; Kraatz, H.-B.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 5865.
6. (a) Wolinski, L.; Tieckelmann, H.; Post, H. W. J. Org. Chem. 1951, 16, 395.
7. (b) Lambert, J. B.; Shulz, W. J., Jr.; McConnell, J. A.; Schilf, W. J. Am. Chem. Soc. 1988, 110, 2201.
8. (a) Wilkinson, G. Inorg. Synth. 1972, 13, 126.
9. 1H NMR data completely analogous to those reported herein for 5; see: Harrod, J. F.; Gilson, D. F. R.; Charles, R. Can. J. Chem. 1969, 47, 2205.
10. (a) Thorn, D. L. Organometallics 1982, 1, 197.
11. 3Si analogs of 6 are fully characterized and exhibit completely analogous spectral data; see: Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017. Aizenberg, M.; Milstein, D. Angew. Chem. 1994, 106, 344; Angew. Chem., Int. Ed. Engl. 1994, 33, 317. Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456.
12. 3Si analogs of 6 are fully characterized and exhibit completely analogous spectral data; see: Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017. Aizenberg, M.; Milstein, D. Angew. Chem. 1994, 106, 344; Angew. Chem., Int. Ed. Engl. 1994, 33, 317. Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456.
13. 3Si analogs of 6 are fully characterized and exhibit completely analogous spectral data; see: Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017. Aizenberg, M.; Milstein, D. Angew. Chem. 1994, 106, 344; Angew. Chem., Int. Ed. Engl. 1994, 33, 317. Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456.
14. 3Si analogs of 6 are fully characterized and exhibit completely analogous spectral data; see: Thorn, D. L.; Harlow, R. L. Inorg. Chem. 1990, 29, 2017. Aizenberg, M.; Milstein, D. Angew. Chem. 1994, 106, 344; Angew. Chem., Int. Ed. Engl. 1994, 33, 317. Aizenberg, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 6456.
15. 3) (11), which was prepared similarly and was fully characterized, exhibited spectral data analogous to those reported herein for 7 and 9; see: Aizenberg, M.; Milstein, D. Science 1994, 265, 359.
16. Ozawa, F.; Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844.
17. (a) Bruce, M. I. J. Chem. Soc. A 1968, 1459.
18. (b) Bennett, R. L.; Bruce, M. I.; Gardner, R. C. F. J. Chem. Soc. Dalton Trans. 1973, 2653.
19. 1H} NMR) after 2 days.
20. Attempts to prepare rhodium analogs of 5 and 6 were unsuccessful.
21. 19F NMR, is known. See, for example: (a) Bennett, R. L.; Bruce, M. I.; Goodfellow. R. J. J. Fluorine Chem. 1972/73, 2, 447. (b) Reference 9b.
22. 19F NMR, is known. See, for example: (a) Bennett, R. L.; Bruce, M. I.; Goodfellow. R. J. J. Fluorine Chem. 1972/73, 2, 447. (b) Reference 9b.
23. For RS-H oxidative additions see, for example: (a) Singer, H.; Wilkinson, G. J. Chem. Soc. A 1968, 2516. (b) Crooks, G. R.; Johnson, B. F. G.; Lewis, J.; Williams, I. G. J. Chem. Soc. A 1969, 797. (c) Stiddard, M. H. B.; Townsend, R. E. J. Chem. Soc. A 1970, 2719. (d) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1975, 97, 3386. (e) Collman, J. P.; Rothrock, R. K.; Stark, R. A. Inorg. Chem. 1977, 16, 437.
24. For RS-H oxidative additions see, for example: (a) Singer, H.; Wilkinson, G. J. Chem. Soc. A 1968, 2516. (b) Crooks, G. R.; Johnson, B. F. G.; Lewis, J.; Williams, I. G. J. Chem. Soc. A 1969, 797. (c) Stiddard, M. H. B.; Townsend, R. E. J. Chem. Soc. A 1970, 2719. (d) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1975, 97, 3386. (e) Collman, J. P.; Rothrock, R. K.; Stark, R. A. Inorg. Chem. 1977, 16, 437.
25. For RS-H oxidative additions see, for example: (a) Singer, H.; Wilkinson, G. J. Chem. Soc. A 1968, 2516. (b) Crooks, G. R.; Johnson, B. F. G.; Lewis, J.; Williams, I. G. J. Chem. Soc. A 1969, 797. (c) Stiddard, M. H. B.; Townsend, R. E. J. Chem. Soc. A 1970, 2719. (d) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1975, 97, 3386. (e) Collman, J. P.; Rothrock, R. K.; Stark, R. A. Inorg. Chem. 1977, 16, 437.
26. For RS-H oxidative additions see, for example: (a) Singer, H.; Wilkinson, G. J. Chem. Soc. A 1968, 2516. (b) Crooks, G. R.; Johnson, B. F. G.; Lewis, J.; Williams, I. G. J. Chem. Soc. A 1969, 797. (c) Stiddard, M. H. B.; Townsend, R. E. J. Chem. Soc. A 1970, 2719. (d) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1975, 97, 3386. (e) Collman, J. P.; Rothrock, R. K.; Stark, R. A. Inorg. Chem. 1977, 16, 437.
27. For RS-H oxidative additions see, for example: (a) Singer, H.; Wilkinson, G. J. Chem. Soc. A 1968, 2516. (b) Crooks, G. R.; Johnson, B. F. G.; Lewis, J.; Williams, I. G. J. Chem. Soc. A 1969, 797. (c) Stiddard, M. H. B.; Townsend, R. E. J. Chem. Soc. A 1970, 2719. (d) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1975, 97, 3386. (e) Collman, J. P.; Rothrock, R. K.; Stark, R. A. Inorg. Chem. 1977, 16, 437.
28. Kuyper, J. Inorg. Chem. 1977, 16, 2171.
29. The reductive elimination of Si-H bonds is well-known, and its kinetics was investigated. See for example: (a) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc., Dalton Trans. 1974, 2311. (b) Hostetler, M. J.; Bergman, R, G. J. Am. Chem. Soc. 1990, 112, 8621. (c) Hostetler, M. J.; Butts, M. D.; Bergman, R. G. Organometallics 1993, 12, 65. (d) Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531. (e) Hays, M. K., Eisenberg, R. Inorg. Chem. 1991, 30, 2623. (f) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297 and references therein.
30. The reductive elimination of Si-H bonds is well-known, and its kinetics was investigated. See for example: (a) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc., Dalton Trans. 1974, 2311. (b) Hostetler, M. J.; Bergman, R, G. J. Am. Chem. Soc. 1990, 112, 8621. (c) Hostetler, M. J.; Butts, M. D.; Bergman, R. G. Organometallics 1993, 12, 65. (d) Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531. (e) Hays, M. K., Eisenberg, R. Inorg. Chem. 1991, 30, 2623. (f) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297 and references therein.
31. The reductive elimination of Si-H bonds is well-known, and its kinetics was investigated. See for example: (a) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc., Dalton Trans. 1974, 2311. (b) Hostetler, M. J.; Bergman, R, G. J. Am. Chem. Soc. 1990, 112, 8621. (c) Hostetler, M. J.; Butts, M. D.; Bergman, R. G. Organometallics 1993, 12, 65. (d) Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531. (e) Hays, M. K., Eisenberg, R. Inorg. Chem. 1991, 30, 2623. (f) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297 and references therein.
32. The reductive elimination of Si-H bonds is well-known, and its kinetics was investigated. See for example: (a) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc., Dalton Trans. 1974, 2311. (b) Hostetler, M. J.; Bergman, R, G. J. Am. Chem. Soc. 1990, 112, 8621. (c) Hostetler, M. J.; Butts, M. D.; Bergman, R. G. Organometallics 1993, 12, 65. (d) Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531. (e) Hays, M. K., Eisenberg, R. Inorg. Chem. 1991, 30, 2623. (f) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297 and references therein.
33. The reductive elimination of Si-H bonds is well-known, and its kinetics was investigated. See for example: (a) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc., Dalton Trans. 1974, 2311. (b) Hostetler, M. J.; Bergman, R, G. J. Am. Chem. Soc. 1990, 112, 8621. (c) Hostetler, M. J.; Butts, M. D.; Bergman, R. G. Organometallics 1993, 12, 65. (d) Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531. (e) Hays, M. K., Eisenberg, R. Inorg. Chem. 1991, 30, 2623. (f) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297 and references therein.
34. The reductive elimination of Si-H bonds is well-known, and its kinetics was investigated. See for example: (a) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc., Dalton Trans. 1974, 2311. (b) Hostetler, M. J.; Bergman, R, G. J. Am. Chem. Soc. 1990, 112, 8621. (c) Hostetler, M. J.; Butts, M. D.; Bergman, R. G. Organometallics 1993, 12, 65. (d) Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531. (e) Hays, M. K., Eisenberg, R. Inorg. Chem. 1991, 30, 2623. (f) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297 and references therein.
35. See, for example: Milstein, D. Acc. Chem. Res. 1984, 17, 221.
36. 5b
37. Herskovitz, T. Inorg. Synth. 1982, 21, 99.
38. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738.
39. 1H NMR, see: Blum, O.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 4582 and references therein.