Si - H activation in titanocene and zirconocene complexes of alkynylsilanes RC≡CSiMe2H (R = tBu, Ph, SiMe3, SiMe2H): A model to understand catalytic reactions of hydrosilanes

Chemistry - A European Journal

Volumn 4, Issue 9, 1998, Pages 1852-1861

  Peulecke, Normen ^a   Ohff, Andreas ^a   Kosse, Peer ^a   Tillack, Annegret ^a   Spannenberg, Anke ^a   Kempe, Rhett ^a   Baumann, Wolfgang ^a   Burlakov, Vladimir V ^a   Rosenthal, Uwe ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Homogeneous catalysis; Si ligands; Si H activation; Titanium; Zirconium

Indexed keywords

EID: 0031665039     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980904)4:9<1852::AID-CHEM1852>3.0.CO;2-E     Document Type: Article

References (53)

1. a) R. D. Miller, J. Michl, Chem. Rev. 1989, 89, 1359;
2. b) Silicon-Based Polymer Science, Advances in Chemistry Series 224, (Eds.: J. M. Ziegler, F. W. G. Fearon), American Chemical Society, Washington, DC, 1990.
3. R. West in The Chemistry of Organic Silicon Compounds, Vol. II (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1989, Chapter 19.
4. C. Aitken, J. F. Harrod, E. Samuel, J. Organomet. Chem. 1985, 279, C11.
5. H. G. Woo, T. D. Tilley, J. Am. Chem. Soc. 1989, 111, 3757.
6. J. Y. Corey X. H. Zhu, T. C. Bedard, L. D. Lange, Organometallics 1991, 10, 924; J. Y. Corey, X. H. Zhu, Organometallics 1992, 11, 672.
7. J. Y. Corey X. H. Zhu, T. C. Bedard, L. D. Lange, Organometallics 1991, 10, 924; J. Y. Corey, X. H. Zhu, Organometallics 1992, 11, 672.
8. S. Bourg, R. J. P. Corriu, M. Enders, J. J. E. Moreau, Organometallics 1995, 14, 564.
9. T. D. Tilley, Acc. Chem. Res. 1993, 26, 22.
10. E. Hengge, M. Weinberger, J. Organomet. Chem. 1993, 443, 167.
11. J. F. Harrod, ACS Symp. Ser. 1988, 360, 89; J. F. Harrod, NATO ASI Ser. E, 1988, 141, 103.
12. J. F. Harrod, ACS Symp. Ser. 1988, 360, 89; J. F. Harrod, NATO ASI Ser. E, 1988, 141, 103.
13. J. P. Banovetz, K. M. Stein, R. M. Waymouth Organometallics 1991, 10, 3430; F. Gauvin, J. F. Harrod, Can. J. Chem. 1990, 68, 1638.
14. J. P. Banovetz, K. M. Stein, R. M. Waymouth Organometallics 1991, 10, 3430; F. Gauvin, J. F. Harrod, Can. J. Chem. 1990, 68, 1638.
15. a) U. Schubert, Adv. Organomet. Chem. 1990, 30, 151;
16. b) U. Schubert, G. Scholz, J. Müller, K. Ackermann, B. Wörle, R. F. D. Stansfield, J. Organomet. Chem. 1986, 306, 303.
17. C. Eaborn, P. N. Kapoor, D. J. Tune, C. L. Turpin, D. R. M. Walton, J. Organomet. Chem. 1973, 63, 323.
18. a) R. J. P. Corriu, J. J. E. Moreau, H. Praet, Organometallics 1990, 9, 2086;
19. b) S. Kotani, T. Matsumoto, H. Yamaguchi, K. Shiina, K. Sonogashira, Chem. Lett. 1989, 293.
20. A. Ohff, P. Kosse, W. Baumann, A. Tillack, R. Kempe, H. Görls, V. V. Burlakov, U. Rosenthal, J. Am. Chem. Soc. 1995, 117, 10399.
21. M. F. Fan, Z. Lin, Organometallics, 1997, 16, 494.
22. a) M. S. Eisen, Rev. Inorg. Chem. 1997, 17, 25;
23. b) R. Beckhaus, Nachr. Chem. Tech. Lab. 1998, 46, 611.
24. L. J. Procopio, P. J. Carroll, D. H. Berry, J. Am. Chem. Soc. 1994, 116, 177.
25. R. Beckhaus, M. Wagner, V. V. Burlakov, W. Baumann, N. Peulecke, A. Spannenberg, R. Kempe, U. Rosenthal, Z. Anorg. Allg. Chem. 1998, 624, 129.
26. J. M. Manriquez, D. R. McAllister, R. D. Sanner, J. E. Bercaw, J. Am. Chem. Soc. 1976, 98, 6733.
27. C. P. Schaller, C. C. Cummins, P. T. Wolczanski, J. Am. Chem. Soc. 1996, 118, 591.
28. J. Yin, J. Klosin, K. A. Abboud, W. M. Jones, J. Am. Chem. Soc. 1995, 117, 3298.
29. M. Trommer, G. E. Miracle, B. E. Eichler, D. E. Powell, R. West, Organometallics 1997, 16, 5737.
30. E. Colomer, R. J. P. Corriu, C. Marzin, A. Vioux, Inorg. Chem. 1982, 21, 368.
31. V. B. Shur, V. V. Burlakov, M. E. Vol'pin, J. Organomet. Chem. 1988, 347, 77.
32. C. Lefeber, A. Ohff, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, H. Görls, J. Organomet. Chem. 1995, 501, 179.
33. V. V. Burlakov, A. Ohff, C. Lefeber, A. Tillack, W. Baumann, R. Kempe, U. Rosenthal, Chem. Ber. 1995, 128, 967.
34. U. Rosenthal, A. Ohff, W. Baumann, R. Kempe, A. Tillack, V. V. Burlakov, Angew. Chem. 1994, 106, 1678; Angew. Chem. Int. Ed. Engl. 1994, 33, 1605.
35. U. Rosenthal, A. Ohff, W. Baumann, R. Kempe, A. Tillack, V. V. Burlakov, Angew. Chem. 1994, 106, 1678; Angew. Chem. Int. Ed. Engl. 1994, 33, 1605.
36. U. Rosenthal, C. Nauck, P. Arndt, S. Pulst, W. Baumann, V. V. Burlakov, H. Görls, J. Organomet. Chem. 1994, 484, 81.
37. A. Ohff, S. Pulst, C. Lefeber, N. Peulecke, P. Arndt, V. V. Burlakov, U. Rosenthal, Synlett 1996, 111.
38. N. Peulecke, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Eur. J. Inorg. Chem. 1998, 419.
39. a) U. Rosenthal, A. Ohff, W. Baumann, A. Tillack, H. Görls, V. V. Burlakov, V. B. Shur, Z. Anorg. Allg. Chem. 1995, 621, 77;
40. b) U. Rosenthal, A. Ohff, M. Michalik, H. Görls, V. V. Burlakov, V. B. Shur, Angew. Chem. 1993, 105, 1228.
41. [20] For Ti-Si derivatives (2.60-2.67 Å) see: a) T. D. Tilley in The Silicon-Heteroatom Bond Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1991, p 309 and references therein. Characteristic Zr-hydride distances were found at about 2 Å. Ti-H range between 1.66 and 1.97 Å for titanium hydride complexes: b) E. Spaltenstein, P. Palma, K. A. Kreutzer, C. A. Willoughby, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 10308, and references therein.
42. [20] For Ti-Si derivatives (2.60-2.67 Å) see: a) T. D. Tilley in The Silicon-Heteroatom Bond Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1991, p 309 and references therein. Characteristic Zr-hydride distances were found at about 2 Å. Ti-H range between 1.66 and 1.97 Å for titanium hydride complexes: b) E. Spaltenstein, P. Palma, K. A. Kreutzer, C. A. Willoughby, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 10308, and references therein.
43. [33c,d]). a) F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 1987, 1-19; b) G. E. Miracle, J. L. Ball, D. R. Powell, R. West, J. Am. Chem. Soc. 1993, 115, 11598; c) T. S. Koloski, P. J. Carroll, D. H. Berry, J. Am. Chem. Soc. 1990, 112, 6405; d) B. K. Campion, R. H. Heyn, T. D. Tilley, J. Am. Chem. Soc. 1993, 115, 5527.
44. [33c,d]). a) F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 1987, 1-19; b) G. E. Miracle, J. L. Ball, D. R. Powell, R. West, J. Am. Chem. Soc. 1993, 115, 11598; c) T. S. Koloski, P. J. Carroll, D. H. Berry, J. Am. Chem. Soc. 1990, 112, 6405; d) B. K. Campion, R. H. Heyn, T. D. Tilley, J. Am. Chem. Soc. 1993, 115, 5527.
45. [33c,d]). a) F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 1987, 1-19; b) G. E. Miracle, J. L. Ball, D. R. Powell, R. West, J. Am. Chem. Soc. 1993, 115, 11598; c) T. S. Koloski, P. J. Carroll, D. H. Berry, J. Am. Chem. Soc. 1990, 112, 6405; d) B. K. Campion, R. H. Heyn, T. D. Tilley, J. Am. Chem. Soc. 1993, 115, 5527.
46. [33c,d]). a) F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 1987, 1-19; b) G. E. Miracle, J. L. Ball, D. R. Powell, R. West, J. Am. Chem. Soc. 1993, 115, 11598; c) T. S. Koloski, P. J. Carroll, D. H. Berry, J. Am. Chem. Soc. 1990, 112, 6405; d) B. K. Campion, R. H. Heyn, T. D. Tilley, J. Am. Chem. Soc. 1993, 115, 5527.
47. H. G. Woo, J. F. Harrod, E. Samuel, Organometallics 1993, 12, 2883.
48. E. D. Jemmis, K. T. Giju, J. Am. Chem. Soc. 1998, 120, 6952.
49. A. Tillack, C. Lefeber, N. Peulecke, D. Thomas, U. Rosenthal, Tetrahedron Lett. 1997, 38, 1533.
50. N. Peulecke, D. Thomas, W. Baumann, C. Fischer, U. Rosenthal, Tetrahedron Lett. 1997, 38, 6655.
51. G. Engelhardt, D. Zeigan, D. Hoebbel, A. Samoson, E. Lippmaa, Z. Chem. 1982, 22, 314.
52. G. M. Sheldrick, Acta Crystallogr. A 1990, 46, 467.
53. G. M. Sheldrick, Universität Göttingen, 1993.