Si-H bond activation of alkynylsilanes by group 4 metallocene complexes

Journal of the American Chemical Society

Volumn 132, Issue 12, 2010, Pages 4369-4380

  Lamač, Martin ^a,b   Spannenberg, Anke ^a   Baumann, Wolfgang ^a   Jiao, Haijun ^a   Fischer, Christine ^a   Hansen, Sven ^a   Arndt, Perdita ^a   Rosenthal, Uwe ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP TRANSFER; ALTERNATIVE ROUTES; DFT CALCULATION; GROUP 4; HAFNOCENE; METALLACYCLES; METALLOCENE COMPLEXES; METHYL GROUP; PRODUCT TYPES; REACTION MECHANISM; SHARP CONTRAST; SI-H BONDS; STERIC REASONS; TITANOCENES;

ACETYLENE; HAFNIUM; MAGNESIUM; ORGANOMETALLICS; SULFUR COMPOUNDS; ZIRCONIUM;

GROUP TECHNOLOGY;

ALKYL GROUP; ALKYNYLSILANE; HAFNIUM; HYDROGEN; METHYL GROUP; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 77950193673     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910527w     Document Type: Article

References (75)

1. Review: (a; Rosenthal, U.; Burlakov, V. V. in Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 355-389.
2. (b) Rosenthal, U.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A. Organometallics 2003, 22, 884.
3. (a) Burlakov, V. V.; Rosenthal, U.; Petrovskii, P. V.; Shur, V. B.; Vol'pin, M. E. Organomet. Chem. USSR 1988, 1, 526.
4. (b) Burlakov, V. V.; Polyakov, A. V.; Yanovsky, A. I.; Struchkov, Y. T.; Shur, V. B.; Vol'pin, M. E.; Rosenthal, U.; Görls, H. J. Organomet. Chem. 1994, 476, 197.
5. Varga, V.; Mach, K.; Polášek, M.; Sedmera, P.; Hiller, J.; Thewalt, U.; Troyanov, S. I. J. Organomet. Chem. 1996, 506, 241.
6. (a) Rosenthal, U.; Ohff, A.; Michalik, M.; Görls, H.; Burlakov, V. V.; Shur, V. B. Angew. Chem., Int. Ed. Engl 1993, 32, 1193.
7. (b) Rosenthal, U.; Ohff, A.; Baumann, W.; Tillack, A.; Görls, H.; Burlakov, V. V.; Shur, V. B. Z. Anorg. Allg. Chem. 1995, 621, 77.
8. (a) Beweries, T.; Burlakov, V. V.; Bach, M. A.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U. Organometallics 2007, 26, 247.
9. (b) Burlakov, V. V.; Beweries, T.; Bogdanov, V. S.; Arndt, P.; Baumann, W.; Petrovskii, P. V.; Spannenberg, A.; Lyssenko, K. A.; Shur, V. B.; Rosenthal, U. Organometallics 2009, 28, 2864.
10. Beweries, T.; Burlakov, V. V.; Bach, M. A.; Peitz, S.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U.; Pathak, B.; Jemmis, E. D. Angew. Chem., Int. Ed. 2007, 46, 6907.
11. (a) Aitken, C. T.; Harrod, J. F.; Samuel, E. J. Organomet. Chem. 1985, 279, C11.
12. (b) Corey, J. Y.; Zhu, X.-H. J. Organomet. Chem. 1992, 439, 1.
13. Shaltout, R. M.; Corey, J. Y. Tetrahedron 1995, 51, 4309.
14. Corey, J. Y.; Zhu, X.-H.; Bedard, T. C.; Lange, L. D. Organometallics 1991, 10, 924.
15. (e) Tilley, T. D. Acc Chem. Res. 1993, 26, 22.
16. (f) Gauvin, F.; Harrod, J. F.; Woo, H.-G. Adv. Organomet. Chem. 1998, 42, 363.
17. (a) Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381.
18. (b) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. J. Am. Chem. Soc 1991, 113, 8564.
19. Corey, J. Y.; Zhu, X.-H. Organometallics 1992, 11, 672.
20. Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095.
21. Takahashi, T.; Bao, F.; Gao, G.; Ogasawara, M. Org. Lett. 2003, 5, 3479.
22. (a) Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784.
23. (b) Tillack, A.; Lefeber, C.; Peulecke, N.; Thomas, D.; Rosenthal, U. Tetrahedron Lett. 1997, 38, 1533.
24. Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642.
25. (a) Hao, L.; Harrod, J. F.; Lebuis, A.-M.; Mu, Y.; Shu, R.; Samuel, E.; Woo, H.-G. Angew. Chem., Int. Ed. 1998, 37, 3126.
26. (b) Harrod, J. F.; Shu, R.; Woo, H.-G.; Samuel, E. Can. J. Chem. 2001, 79, 1075.
27. (a) Campion, B. K.; Falk, J.; Tilley, T. D. J. Am. Chem. Soc. 1987, 109, 2049.
28. (b) Eisner, F. H.; Tilley, T. D.; Rheingold, A. L.; Geib, S. J. J. Organomet. Chem. 1988, 358, 169.
29. (a) Woo, H.-G.; Tilley, T. D. J. Am. Chem. Soc. 1989, 111, 3757.
30. (b) Woo, H.-G.; Tilley, T. D. J. Am. Chem. Soc. 1989, 111, 8043.
31. (c) Woo, H.-G.; Heyn, R. H.; Tilley, T. D. J. Am. Chem. Soc. 1992, 114, 5698.
32. (d) Woo, H.-G.; Walzer, J. F.; Tilley, T. D. J. Am. Chem. Soc. 1992, 114, 7047.
33. (e) Casty, G. L.; Lugmair, C. G.; Radu, N. S.; Tilley, T. D.; Walzer, J. F.; Zargarian, D. Organometallics 1997, 16, 8.
34. (f) Sadow, A. D.; Tilley, T. D. J. Am. Chem. Soc. 2002, 124, 6814.
35. (g) Sadow, A. D.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 9462.
36. Nevertheless, compounds with group 4 metal-silicon bonds were reported as early as the 1960s: Cardin, D. J.; Keppie, S. A.; Kingston, B. M.; Lappert, M. F. Chem. Commun. 1967, 1035. For other examples, see refs 11-21.
37. (a) Rösch, L.; Altnau, G.; Erb, W.; Pickardt, J.; Bruncks, N. J. Organomet. Chem. 1980, 197, 51.
38. (b) Tilley, T. D. Organometallics 1985, 4, 1452.
39. Kreutzer, K. A.; Fischer, R. A.; Davis, W. M.; Spaltenstein, E.; Buchwald, S. L. Organometallics 1991, 10, 4031.
40. Spaltenstein, E.; Palma, P.; Kreutzer, K. A.; Willoughby, C. A.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 10308.
41. Aitken, C. T.; Harrod, J. T.; Samuel, E. J. Am. Chem. Soc. 1986, 108, 4059.
42. (a) Aitken, C. T.; Harrod, J. T.; Samuel, E. Can. J. Chem. 1986, 64, 1677.
43. (b) Mu, Y.; Aitken, C.; Cote, B.; Harrod, J. F.; Samuel, E. Can. J. Chem. 1991, 69, 264.
44. Samuel, E.; Mu, Y.; Harrod, J. F.; Dromzee, Y.; Jeannin, Y. J. Am. Chem. Soc. 1990, 112, 3435.
45. Hao, L.; Woo, H.-G.; Lebuis, A.-M.; Samuel, E.; Harrod, J. F. Chem. Commun. 1998, 2013.
46. (a) Ohff, A.; Kosse, P.; Baumann, W.; Tillack, A.; Kempe, R.; Görls, H.; Burlakov, V. V.; Rosenthal, U. J. Am. Chem. Soc. 1995, 117, 10399.
47. (b) Peulecke, N.; Ohff, A.; Kosse, P.; Tillack, A.; Spannenberg, A.; Kempe, R.; Baumann, W.; Burlakov, V. V.; Rosenthal, U. Chem. Eur. J. 1998, 4, 1852.
48. Fan, M.-F.; Lin, Z. Organometallics 1997, 16, 494.
49. An alternative approach leading to such compounds will be described elsewhere: Lamač, M.; Spannenberg, A.; Jiao, H.; Hansen, S.; Baumann, W.; Arndt, P.; Rosenthal, U. Angew. Chem., Int. Ed., in press.
50. Petasis, N. A.; Fu, D.-K. Organometallics 1993, 12, 3776.
51. Doxsee, K. M.; Juliette, J. J. J.; Mouser, J. K. M.; Zientara, K. Organometallics 1993, 12, 4682.
52. The reductive elimination of silyl groups from titanocene was recently reported: Zirngast, M.; Flörke, U.; Baumgartner, J.; Marschner, C. Chem. Commun. 2009, 5538.
53. The product was identified by NMR spectroscopy. For references, see: Marsella, J. A.; Huffman, J. C.; Folting, K.; Caulton, K. G. Inorg. Chim. Acta 1985, 96, 161.
54. Dioumaev, V. K.; Harrod, J. F. Organometallics 1997, 16, 1452.
55. See the Supporting Information for details.
56. (a) Atwood, J. L.; Hunter, W. E.; Rausch, M. D. J. Am. Chem. Soc. 1976, 98, 2454.
57. (b) Sabada, M. B.; Farona, M. F.; Zarate, E. A.; Youngs, W. J. J. Organomet. Chem. 1988, 338, 347.
58. (c) Yousaf, S. M.; Farona, M. F.; Shively, R. J.; Youngs, W. J. J. Organomet. Chem. 1989, 363, 281.
59. Kempe, R.; Spannenberg, A.; Kosse, P.; Peulecke, N.; Rosenthal, U. Z. Kristallogr.-New Cryst. Struct. 1998, 213, 789.
60. Rüdinger, C.; Bissinger, P.; Beruda, H.; Schmidbaur, H. Organometallics 1992, 11, 2867.
61. Angles between centroid-centroid vector and normal to the respective plane.
62. 3 has also been reported: Sadow, A. D.; Tilley, T. D. Organometallics 2003, 22, 3577.
63. Yin, J.; Klosin, J.; Abboud, K. A.; Jones, W. M. J. Am. Chem. Soc. 1995, 117, 3298.
64. (a) Mori, M.; Kuroda, S.; Dekura, F. J. Am. Chem. Soc. 1999, 121, 5591.
65. (b) Kuroda, S.; Dekura, F.; Sato, Y.; Mori, M. J. Am. Chem. Soc. 2001, 123, 4139.
66. Mori, M. Top. Organomet. Chem. 2005, 10, 41.
67. 11b,18
68. 29
69. Wailes, P. C.; Weigold, H.; Bell, A. P. J. Organomet. Chem. 1972, 34, 155.
70. (a) Ruffolo, R.; Decken, A.; Girard, L.; Gupta, H. K.; Brook, M. A.; McGlinchey, M. J. Organometallics 1994, 13, 4328.
71. (b) Wrackmeyer, B.; Kehr, G.; Süss, J.; Molla, E. J. Organomet. Chem. 1998, 562, 207.
72. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112.
73. Brandenburg, K. DIAMOND, Version 3.1e; Crystal Impact GbR, Bonn, Germany, 2007.
74. Frisch, M. J. et al.; Gaussian 03, Revision D.Ol; Gaussian, Inc.: Wallingford, CT, 2004.
75. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.