Stoichiometric and catalytic behavior of cationic silyl and silylene complexes

Organometallics

Volumn 21, Issue 22, 2002, Pages 4648-4661

  Klei, Steven R ^a,b   Tilley, T Don ^a,b   Bergman, Robert G ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACIDS;

CATALYSIS; CHEMICAL BONDS; KETONES; STOICHIOMETRY;

COMPLEXATION;

EID: 0037662094     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0203173     Document Type: Article

References (57)

1. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; Wiley-Interscience: New York, 1994.
2. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science: Sausalito, CA, 1987.
3. Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887.
4. Dioumaev, V. K.; Plossl, K.; Carroll, P. J.; Berry, D. H. J. Am. Chem. Soc. 1999, 121, 8391.
5. Reed, C. A. Acc. Chem. Res. 1998, 31, 133 and references therein.
6. Chen, E. Y. X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
7. Thayer, A. M. Chem. Eng. News 1995, 73, 15.
8. Reinartz, S.; White, P. S.; Brookhart, M.; Templeton, J. L. Organometallics 2001, 20, 1709.
9. Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848.
10. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970.
11. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462.
12. Klei, S. R.; Golden, J. T.; Burger, P.; Bergman, R. G. J. Mol. Catal. A 2002, accepted for publication.
13. Tellers, D. M.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 954.
14. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley-Interscience: New York, 2000.
15. Esteruelas, M. A.; Nurnberg, O.; Olivan, M.; Oro, L. A.; Werner, H. Organometallics 1993, 12, 3264.
16. Okazaki, M.; Tobita, H.; Kawano, Y.; Inomata, S.; Ogino, H. J. Organomet. Chem. 1998, 553, 1.
17. Mitchell, G. P.; Tilley, T. D.; Yap, G. P. A.; Rheingold, A. L. Organometallics 1995, 14, 5472.
18. Straus, D. A.; Grumbine, S. D.; Tilley, T. D. J. Am. Chem. Soc. 1990, 112, 7801.
19. Feldman, J. D.; Mitchell, G. P.; Nolte, J. O.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 11184.
20. Klei, S. R.; Tilley, T. D.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 1816.
21. Peters, J. C.; Feldman, J. D.; Tilley, T. D. J. Am. Chem. Soc. 1999, 121, 9871.
22. Wanandi, P. W.; Glaser, P. B.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 972.
23. Mork, B. V.; Tilley, T. D. J. Am. Chem. Soc. 2001, 123, 9702.
24. Ueno, K.; Asami, S.; Watanabe, N.; Ogino, H. Organometallics 2002, 21, 1326.
25. Mork, B. V.; Tilley, T. D. Manuscript in preparation.
26. Mitchell, G. P.; Tilley, T. D. J. Am. Chem. Soc. 1997, 119, 11236.
27. Zhang, C.; Grumbine, S. D.; Tilley, T. D. Polyhedron 1991, 10, 1173.
28. Grumbine, S. K.; Mitchell, G. P.; Straus, D. A.; Tilley, T. D. Organometallics 1998, 17, 5607.
29. Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151.
30. LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906.
31. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988.
32. Ozawa, F.; Kamite, J. Organometallics 1998, 17, 5630.
33. Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793.
34. Klei, S. R.; Tilley, T. D.; Bergman R. G. Submitted for publication.
35. Oldham, W. J.; Hinkle, A. S.; Heinekey, D. M. J. Am. Chem. Soc. 1997, 119, 11028.
36. Klei, S. R.; Tilley, T. D.; Bergman, R. G. Organometallics 2001, 20, 3220.
37. This experiment was inspired by a similar observation made by F.L. Taw in the corresponding cationic rhodium system. See: Taw, F. L.; Brookhart, M.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 4192.
38. Golden, J. T. Ph.D. Thesis, University of California, Berkeley, 2001.
39. Hollis, T. K.; Robinson, N. P.; Rosnich, B. Tetrahedron Lett. 1992, 33, 6423.
40. Grumbine, S. K.; Straus, D. A.; Tilley, T. D.; Rheingold, A. L. Polyhedron 1995, 14, 127.
41. Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090.
42. A referee has suggested an alternative mechanism involving coordination of p-tolualdehyde through its oxygen to the silylene ligand of 4, followed by hydride migration to the carbonyl carbon of the aldehyde to give intermediate III. We cannot rule out this possibility on the basis of our observations at the present time.
43. Cundari, T. R.; Gordon, M. S. J. Phys. Chem. 1993, 96, 631.
44. Arnold, F. P. Organometallics 1999, 18, 4800.
45. Berry, D. H.; Procopio, L. J. J. Am. Chem. Soc. 1989, 117, 4099.
46. Golden, J. T.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 5837.
47. Klei, S. R.; Golden, J. T.; Tilley, T. D.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 2092.
48. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305.
49. Han, Y.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 5939.
50. Niu, S.; Zaric, S.; Bayse, C. A.; Strout, D. L.; Hall, M. B. Organometallics 1998, 17, 5139.
51. Reed, C. A. Acc. Chem. Res. 1998, 31, 325.
52. (a) Lambert, J. B.; Zhao, Y. Angew. Chem., Int. Ed. 1997, 36, 400.
53. (b) For an additional recently-published example, see: Kim, K.C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 825.
54. Procopio, L. J.; Berry, D. H. J. Am. Chem. Soc. 1991, 113,4039.
55. Reichl, J. A.; Popoff, C. M.; Gallagher, L. A.; Remsen, E. E.; Berry, D. H. J. Am. Chem. Soc. 1996, 118, 9430.
56. Alaimo, P. J.; Peters, D. W.; Arnold, J.; Bergman, R. G. J. Chem. Educ. 2001, 78, 64.
57. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274.