Exploiting catalytic dehydrogenative coupling in the synthesis and study of polysilanes

Macromolecular Symposia

Volumn 196, Issue , 2003, Pages 347-353

  Rosenberg, Lisa ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

Catalysis; Functionalization of polymers; Oligomers; Polysilanes; Transition metal chemistry

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; CORRELATION METHODS; DEHYDROGENATION; SYNTHESIS (CHEMICAL);

DEHYDROGENATIVE COUPLING;

POLYSILANES;

DIMETICONE; SILANE DERIVATIVE; SILICON; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DERIVATIZATION; HYDROGEN BOND; POLYMERIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0041845323     PISSN: 10221360     EISSN: None     Source Type: Journal    
DOI: 10.1002/masy.200390173     Document Type: Article

References (35)

1. Examples of the preparation of functionalized oligosilanes include: (a) K. H. Pannell, J. M. Rozell, C. Hernandez, J. Am. Chem. Soc. 1989, 111, 4482; (b) J. Y. Corey, D. M. Kraichely, J. L. Huhmann, J. Braddock-Wilking, A. Lindeberg, Organometallics 1995, 14, 2704; (c) H. Sakurai, Y. Eriyama, Y. Kamiyama, Y. Nakadaira, J. Organomet. Chem 1984, 264, 229; (d) J. Zech, H. Schmidbaur, Chem. Ber. 1990, 123, 2087; (e) M. Söldner, A. Schier, H. Schmidbaur, J. Organomet. Chem. 1996, 521, 295
2. Examples of the preparation of functionalized oligosilanes include: (a) K. H. Pannell, J. M. Rozell, C. Hernandez, J. Am. Chem. Soc. 1989, 111, 4482; (b) J. Y. Corey, D. M. Kraichely, J. L. Huhmann, J. Braddock-Wilking, A. Lindeberg, Organometallics 1995, 14, 2704; (c) H. Sakurai, Y. Eriyama, Y. Kamiyama, Y. Nakadaira, J. Organomet. Chem 1984, 264, 229; (d) J. Zech, H. Schmidbaur, Chem. Ber. 1990, 123, 2087; (e) M. Söldner, A. Schier, H. Schmidbaur, J. Organomet. Chem. 1996, 521, 295
3. Examples of the preparation of functionalized oligosilanes include: (a) K. H. Pannell, J. M. Rozell, C. Hernandez, J. Am. Chem. Soc. 1989, 111, 4482; (b) J. Y. Corey, D. M. Kraichely, J. L. Huhmann, J. Braddock-Wilking, A. Lindeberg, Organometallics 1995, 14, 2704; (c) H. Sakurai, Y. Eriyama, Y. Kamiyama, Y. Nakadaira, J. Organomet. Chem 1984, 264, 229; (d) J. Zech, H. Schmidbaur, Chem. Ber. 1990, 123, 2087; (e) M. Söldner, A. Schier, H. Schmidbaur, J. Organomet. Chem. 1996, 521, 295
4. Examples of the preparation of functionalized oligosilanes include: (a) K. H. Pannell, J. M. Rozell, C. Hernandez, J. Am. Chem. Soc. 1989, 111, 4482; (b) J. Y. Corey, D. M. Kraichely, J. L. Huhmann, J. Braddock-Wilking, A. Lindeberg, Organometallics 1995, 14, 2704; (c) H. Sakurai, Y. Eriyama, Y. Kamiyama, Y. Nakadaira, J. Organomet. Chem 1984, 264, 229; (d) J. Zech, H. Schmidbaur, Chem. Ber. 1990, 123, 2087; (e) M. Söldner, A. Schier, H. Schmidbaur, J. Organomet. Chem. 1996, 521, 295
5. Examples of the preparation of functionalized oligosilanes include: (a) K. H. Pannell, J. M. Rozell, C. Hernandez, J. Am. Chem. Soc. 1989, 111, 4482; (b) J. Y. Corey, D. M. Kraichely, J. L. Huhmann, J. Braddock-Wilking, A. Lindeberg, Organometallics 1995, 14, 2704; (c) H. Sakurai, Y. Eriyama, Y. Kamiyama, Y. Nakadaira, J. Organomet. Chem 1984, 264, 229; (d) J. Zech, H. Schmidbaur, Chem. Ber. 1990, 123, 2087; (e) M. Söldner, A. Schier, H. Schmidbaur, J. Organomet. Chem. 1996, 521, 295
6. See for example: H. J. S. Winkler, H. Gilman, J. Org. Chem. 1961, 26, 1265.
7. (a) T. D. Tilley, Comments Inorg. Chem. 1990, 10, 37;
8. (b) J. Y. Corey, in: "Dehydrogenative Coupling Reactions of Hydrosilanes", G. L. Larson, Ed., JAI Press Inc., 1991. Vol. 1, 327;
9. (c) F. Gauvin, J. F. Harrod, H. G. Woo, Adv. Organomet. Chem. 1998, 42, 363;
10. (d) J. A. Reichl, D. H. Berry, Adv. Organomet. Chem. 1999, 43, 197.
11. An exception is the reported activity of a Pt catalyst in the coupling of 3° silanes to hexa-organosubstituted disilanes. M. Tanaka, T. Kobayashi, T. Hayashi, T. Sakakura, Appl. Organomet. Chem. 1988, 2, 91.
12. (a) T. Imori, T. D. Tilley, Polyhedron 1994, 13, 2231;
13. (b) V. K. Dioumaev, J. F. Harrod, J. Organomet. Chem. 1996, 521, 133.
14. 2 has been reported, but requires the presence of cyclic olefins, which are hydrogenated in tandem with the coupling process. Complex product mixtures result, which include hydrosilation products. J. Y. Corey, X.-H. Zhu, Organometallics 1992, 11, 672.
15. M. D. Curtis, P. S. Epstein, Adv. Organomet. Chem. 1981, 19, 213.
16. See for example (a) M. D. Fryzuk, L. Rosenberg, S. J. Rettig, Inorg. Chim. Acta 1994, 222, 345. There are very few reports of late metal activities for the production of longer (DP>6) silicon chains. These include: (b) B. P. S. Chauhan, T. Shimizu, M. Tanaka, Chem. Lett. 1997, 785; (c) F.-G. Fontaine, T. Kadkhodazadeh, D. Zargarian, Chem. Commun. 1998, 1253.
17. See for example (a) M. D. Fryzuk, L. Rosenberg, S. J. Rettig, Inorg. Chim. Acta 1994, 222, 345. There are very few reports of late metal activities for the production of longer (DP>6) silicon chains. These include: (b) B. P. S. Chauhan, T. Shimizu, M. Tanaka, Chem. Lett. 1997, 785; (c) F.-G. Fontaine, T. Kadkhodazadeh, D. Zargarian, Chem. Commun. 1998, 1253.
18. See for example (a) M. D. Fryzuk, L. Rosenberg, S. J. Rettig, Inorg. Chim. Acta 1994, 222, 345. There are very few reports of late metal activities for the production of longer (DP>6) silicon chains. These include: (b) B. P. S. Chauhan, T. Shimizu, M. Tanaka, Chem. Lett. 1997, 785; (c) F.-G. Fontaine, T. Kadkhodazadeh, D. Zargarian, Chem. Commun. 1998, 1253.
19. The reactivity of I and other Rh(I) phosphine complexes for dehydrocoupling of silanes, albeit invariably accompanied by redistribution reactions, was already established. (a) I. Ojima, S.-I. Inaba, T. Kogure, J. Organomet. Chem. 1973, 55, C7; (b) M. F. Lappert, R. K. Maskell, J. Organomet. Chem. 1984, 264, 217; (c) J. Y. Corey, L. S. Chang, E. R. Corey, Organometallics 1987, 6, 1595; (d) K. A. Brown-Wensley, Organometallics 1987, 6, 1590; (e) L. Rosenberg, M. D. Fryzuk, S. J. Rettig, Organometallics 1999, 18, 958.
20. The reactivity of I and other Rh(I) phosphine complexes for dehydrocoupling of silanes, albeit invariably accompanied by redistribution reactions, was already established. (a) I. Ojima, S.-I. Inaba, T. Kogure, J. Organomet. Chem. 1973, 55, C7; (b) M. F. Lappert, R. K. Maskell, J. Organomet. Chem. 1984, 264, 217; (c) J. Y. Corey, L. S. Chang, E. R. Corey, Organometallics 1987, 6, 1595; (d) K. A. Brown-Wensley, Organometallics 1987, 6, 1590; (e) L. Rosenberg, M. D. Fryzuk, S. J. Rettig, Organometallics 1999, 18, 958.
21. The reactivity of I and other Rh(I) phosphine complexes for dehydrocoupling of silanes, albeit invariably accompanied by redistribution reactions, was already established. (a) I. Ojima, S.-I. Inaba, T. Kogure, J. Organomet. Chem. 1973, 55, C7; (b) M. F. Lappert, R. K. Maskell, J. Organomet. Chem. 1984, 264, 217; (c) J. Y. Corey, L. S. Chang, E. R. Corey, Organometallics 1987, 6, 1595; (d) K. A. Brown-Wensley, Organometallics 1987, 6, 1590; (e) L. Rosenberg, M. D. Fryzuk, S. J. Rettig, Organometallics 1999, 18, 958.
22. The reactivity of I and other Rh(I) phosphine complexes for dehydrocoupling of silanes, albeit invariably accompanied by redistribution reactions, was already established. (a) I. Ojima, S.-I. Inaba, T. Kogure, J. Organomet. Chem. 1973, 55, C7; (b) M. F. Lappert, R. K. Maskell, J. Organomet. Chem. 1984, 264, 217; (c) J. Y. Corey, L. S. Chang, E. R. Corey, Organometallics 1987, 6, 1595; (d) K. A. Brown-Wensley, Organometallics 1987, 6, 1590; (e) L. Rosenberg, M. D. Fryzuk, S. J. Rettig, Organometallics 1999, 18, 958.
23. The reactivity of I and other Rh(I) phosphine complexes for dehydrocoupling of silanes, albeit invariably accompanied by redistribution reactions, was already established. (a) I. Ojima, S.-I. Inaba, T. Kogure, J. Organomet. Chem. 1973, 55, C7; (b) M. F. Lappert, R. K. Maskell, J. Organomet. Chem. 1984, 264, 217; (c) J. Y. Corey, L. S. Chang, E. R. Corey, Organometallics 1987, 6, 1595; (d) K. A. Brown-Wensley, Organometallics 1987, 6, 1590; (e) L. Rosenberg, M. D. Fryzuk, S. J. Rettig, Organometallics 1999, 18, 958.
24. L. Rosenberg, C. W. Davis, J. Yao, J. Am. Chem. Soc. 2001, 123, 5120.
25. P. Burger, R. G. Bergman, J. Am. Chem. Soc. 1993, 115, 10462.
26. The debate centres around whether a metal silylene ("M=Si") intermediate is involved in (or required for) Si-Si bond formation, or whether oxidative addition and reductive elimination steps involving only M-Si single bonds can be responsible for Si-Si coupling. See Reference 5.
27. n-H, have resulted either in low or incomplete substitution (Reference 15b) or in significant polymer degradation. (References 15c,d). (a) D. J. Harrison, L. Rosenberg, unpublished results; (b) J. P. Banovetz, Y.-L. Hsiao, R. M. Waymouth, J. Am. Chem. Soc. 1993, 115, 2540; (c) Reference 3a; (d) D. M. Friesen, R. McDonald, L. Rosenberg, Can. J. Chem. 1999, 77, 1931.
28. n-H, have resulted either in low or incomplete substitution (Reference 15b) or in significant polymer degradation. (References 15c,d). (a) D. J. Harrison, L. Rosenberg, unpublished results; (b) J. P. Banovetz, Y.-L. Hsiao, R. M. Waymouth, J. Am. Chem. Soc. 1993, 115, 2540; (c) Reference 3a; (d) D. M. Friesen, R. McDonald, L. Rosenberg, Can. J. Chem. 1999, 77, 1931.
29. n-H, have resulted either in low or incomplete substitution (Reference 15b) or in significant polymer degradation. (References 15c,d). (a) D. J. Harrison, L. Rosenberg, unpublished results; (b) J. P. Banovetz, Y.-L. Hsiao, R. M. Waymouth, J. Am. Chem. Soc. 1993, 115, 2540; (c) Reference 3a; (d) D. M. Friesen, R. McDonald, L. Rosenberg, Can. J. Chem. 1999, 77, 1931.
30. n-H, have resulted either in low or incomplete substitution (Reference 15b) or in significant polymer degradation. (References 15c,d). (a) D. J. Harrison, L. Rosenberg, unpublished results; (b) J. P. Banovetz, Y.-L. Hsiao, R. M. Waymouth, J. Am. Chem. Soc. 1993, 115, 2540; (c) Reference 3a; (d) D. M. Friesen, R. McDonald, L. Rosenberg, Can. J. Chem. 1999, 77, 1931.
31. J. Yao, L. Rosenberg, unpublished results.
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34. (a) D. J. Harrison, L. Rosenberg, unpublished results.
35. 2 in the presence of catalytic amounts of Cul; A. Kunai, T. Kawakami, A. Toyoda, M. Ishikawa, Organometallics 1992, 11, 2708.