A pentagonal pyramidal zirconium imido complex for catalytic hydroamination of unactivated alkenes

Organometallics

Volumn 25, Issue 17, 2006, Pages 4069-4071

  Thomson, Robert K ^a   Bexrud, Jason A ^a   Schafer, Laurel L ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; AMINATION; CATALYSIS; COMPLEXATION; MOLECULAR STRUCTURE; OLEFINS;

AMIDATES; CATALYTIC HYDROAMINATION; PYRAMIDAL GEOMETRY; ZIRCONIUM IMIDO COMPLEX;

ZIRCONIUM COMPOUNDS;

EID: 33748323491     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060545n     Document Type: Article

References (45)

1. (a) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
2. (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
3. (c) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
4. (d) Roesky, P. W.; Muller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708.
5. (e) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748.
6. (f) Michael, F. E.; Cochran, B. M. J. Am. Chem. Soc. 2006, 128, 4246 and references therein.
7. (a) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
8. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
9. (c) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
10. (d) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923.
11. (e) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475.
12. (f) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305.
13. (g) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961.
14. (h) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541.
15. (i) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967.
16. (j) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839.
17. (k) Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956 and references therein.
18. Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632.
19. (a) Gribkov, D. V.; Hultzsch, K. C. Angew. Chem., Int. Ed. 2004, 43, 5542.
20. (b) Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894.
21. (a) Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
22. (b) See Figure 5 in the Supporting Information for the catalytic cycle.
23. (a) Bexrud, J. A.; Beard, J. D.; Leitch, D. C.; Schafer, L. L. Org. Lett. 2005, 7, 1959.
24. (b) Kim, H.; Lee, P. H.; Livinghouse, T. Chem. Commun. 2005, 5205.
25. (c) For the proposed catalytic cycle see Figure 4 in the Supporting Information.
26. (a) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 8729.
27. (b) Hoyt, H. M.; Michael, F. E.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 1018.
28. (c) Cummins, C. C.; Baxter, S. M.; Wolczanski, P. T. J. Am. Chem. Soc. 1988, 110, 8731.
29. (d) Cummins, C. C.; Schaller, C. P.; Duyne, G. D. V.; Wolczanski, P. T.; Chan, A. W. E.; Hoffmann, R. J. Am. Chem. Soc. 1991, 113, 2985.
30. (e) Li, Y.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2004, 126, 1794.
31. (f) Basuli, F.; Bailey, B. C.; Watson, L. A.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. Organometallics 2005, 24, 1886.
32. (g) Mountford, P. Chem. Commun. 1997, 2127.
33. (h) Hazari, N.; Mountford, P. Acc. Chem. Res. 2005, 38, 839.
34. (i) Kissounko, D. A.; Guzei, I. A.; Gellman, S. H.; Stahl, S. S. Organometallics 2005, 24, 5208.
35. (j) Basuli, F.; Aneetha, H.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2005, 127, 17992.
36. (k) Kissounko, D. A.; Epshteyn, A.; Fettinger, J. C.; Sita, L. R. Organometallics 2006, 25, 1076 and references therein.
37. (a) Li, C.; Thomson, R. K.; Gillon, B.; Patrick, B. O.; Schafer, L. L. Chem. Commun. 2003, 2462.
38. (b) Zhang, Z.; Schafer, L. L. Org. Lett. 2003, 5, 4733.
39. (c) Ayinla, R. O.; Schafer, L. L. Inorg. Chim. Acta 2006, 359, 3097.
40. This trend has been seen previously with cationic group 4 catalysts.
41. (a) See the Supporting Information for details, (b) For full crystallographic details, see the Supporting Information, (c) See the Supporting Information for kinetic details, (d) For a kinetic plot see Figure 22 in the Supporting Information.
42. Thomson, R. K.; Zahariev, F. E.; Zhang, Z.; Patrick, B. O.; Wang, Y. A.; Schafer, L. L. Inorg. Chem. 2005, 44, 8680.
43. Blum, S. A.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 2003, 125, 14276.
44. Anderson, L. L.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc. 2005, 127, 14542.
45. We cannot rule out the conversion of an imido species to a catalytically active bis(amido) species that can subsequently catalyze hydroamination via a σ-bond insertion process.