Investigation of the regioselectivity of alkene hydrosilylation catalyzed by organolanthanide and group 3 metallocene complexes

Organometallics

Volumn 17, Issue 17, 1998, Pages 3754-3758

  Molander, Gary A ^a   Dowdy, Eric D ^a   Noll, Bruce C ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001372884     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980279g     Document Type: Article

References (57)

1. Molander, G. A. Chemtracts 1998, 11, 237.
2. (a) Marks T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson G., Stone, F. G. A., Abel E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 3, Chapter 21.
3. (b) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51.
4. (c) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 4, Chapter 2.
5. (d) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247.
6. (a) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111.
7. (b) Molander, G. A.; Hoberg, J. O. J. Org. Chem. 1992, 57, 3266.
8. (c) Haar, C. M. Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765.
9. (d) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks T. J. Organometallics 1997, 16, 4486.
10. (e) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705.
11. (f) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
12. (a) Fu, P. F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157
13. (b) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
14. (c) Molander, G. A.; Retsch, W. H. Organometallics 1995, 14, 4570.
15. (d) Molander, G. A.; Nichols, P. J. J. Org. Chem. 1996, 61, 6040.
16. (e) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1996, 524, 275.
17. (f) Molander, G. A.; Retsch, W. H. J. Am. Chem. Soc. 1997, 119, 8817.
18. (g) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347.
19. (h) Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
20. (i) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40.
21. (j) Molander, G. A.; Nichols, P. J. J. Org. Chem. 1998, 63, 2292.
22. (k) Watson, P. L.; Tebbe, F. N. U.S. Patent 4,965,386; Chem. Abstr. 1991, 114, 123331p.
23. (l) Molander, G. A.; Dowdy, E. D.; Schumann, H. J. Org. Chem. 1998, 63, 3386.
24. (a) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
25. (b) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks T. J. J. Am. Chem. Soc. 1994, 116, 10241.
26. (c) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770.
27. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295.
28. (e) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757.
29. (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 8 Chapter 3.12.
30. (b) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Chapter 25.
31. (a) Speier, J. L. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17.
32. (b) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
33. (c) Prignano, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1974, 109, 3586.
34. (a) Choo, K. Y.; Gaspar, P. P. J. Am. Chem. Soc. 1974, 96, 1284.
35. (b) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1995, 36, 2875.
36. Nozakura, S.; Konotsune, S. Bull. Chem. Soc. Jpn. 1956, 29, 322.
37. Widenhoefer, R. A.; DeCarli, M. A. J. Am. Chem. Soc. 1998, 120, 3805.
38. Kobrakov, K. I.; Chernysheva, T. I.; Nametkin, N. S. Dolk. Akad. Nauk SSSR 1971, 798, 1340.
39. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1649.
40. (b) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2121.
41. (c) Taber, D. F.; Yet, L.; Bhamidipati, R. S. Tetrahedron Lett. 1995, 36, 351.
42. (d) Fleming, I.; Hennings, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
43. (e) Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229.
44. (f) Fleming, I.; Winter, S. B. D. Tetrahedron Lett. 1993, 34, 7287.
45. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
46. 3 showed no indication of H/D scrambling, indicating the irreversible nature of the olefin insertion step. See refs 4a and 4g.
47. 22
48. 3+ (1.019 Å). See: Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
49. 1H FT-NMR Spectra; Aldrich Chemical: Milwaukee, 1992.
50. Evans, W. J.; Meadows, J. H.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1984, 106, 1291.
51. Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091.
52. (a) (Ln = Lu) Voskoboynikov, A. Z.; Parshina, I. N.; Shetstakova, A. K. Butin, K. P.; Beletskaya, I. P.; Kuz'mina, L. G.; Howard, J. A. K. Organometallics 1997, 16, 4041.
53. (b) (Ln = Y, Sm) Keitsch, M. Unpublished results.
54. Schumann, H.; Genthe, W.; Bruncks, N.; Pickardt, J. Organometallics 1982, 1, 1194.
55. Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103.
56. Stern, D.; Sabat, M.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 9558.
57. Bunel, E. E. Ph.D. Thesis, California Institute of Technology, 1989.