Selective transformations of organic compounds by imidozirconocene complexes

Chemical Record

Volumn 2, Issue 6, 2002, Pages 431-445

  Duncan, Andrew P ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

C H activation; Cycloaddition; Hydroamination; Imido; Imine metathesis; Kinetic resolution

Indexed keywords

4 AMINOBUTYRIC ACID; ALKENE; ALKYNE; AZIDE; IMINE; NITROGEN; ORGANIC COMPOUND; ORGANOMETALLIC COMPOUND; ZIRCONIUM; ZIRCONOCENE DICHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ALKENES; ALKYNES; AZIDES; CATALYSIS; GAMMA-AMINOBUTYRIC ACID; IMINES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROGEN; ORGANIC CHEMICALS; ORGANOMETALLIC COMPOUNDS; ZIRCONIUM;

EID: 0942284621     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.10039     Document Type: Article

References (56)

1. Nugent, W.A.; Mayer, J.M. Metal-Ligand Multiple Bonds; John Wiley and Sons: New York, 1988.
2. Wigley, D.E. Prog Inorg Chem 1994, 42, 239.
3. Nugent, W.A.; Harlow, R.L. Inorg Chem 1979, 18, 2030.
4. Walsh, P.J.; Hollander, F.J.; Bergman, R.G. J Am Chem Soc 1988, 110, 8729.
5. Cummins, C.C.; Baxter, S.M.; Wolczanski, P.T. J Am Chem Soc 1988, 110, 8731.
6. Walsh, P.J.; Hollander, F.J.; Bergman, R.G. Organometallics 1993, 12, 3705.
7. Zuckermann, R.L.; Krska, S.W.; Bergman, R.G. J Am Chem Soc 2000, 122, 751.
8. Sweeney, Z.K.; Salsman, J.L.; Andersen, R.A.; Bergman, R.G. Angew Chem Intl Ed 2000, 39, 2339.
9. Lauher, J.W.; Hoffmann, R. J Am Chem Soc 1976, 98, 1729.
10. While care must be taken in rationalizing metric data of THF-solvated imidozirconocene complexes with molecular orbitals derived for more symmetric nonsolvated complexes, we feel that the qualitative arguments presented here are not compromised by such a simplification. For quantitative molecular orbital treatments of related compounds, see (a) Jorgensen, K.A. Inorg Chem 1993, 1521.
11. (b) Osborne, J.H.; Rheingold, A.L.; Trogler, W.C. J Am Chem Soc 1985, 7945.
12. (c) Green, J.C.; Green, M.L.H.; James, J.T.; Konidaris, P.C.; Maunder, G.H.; Mountford, P.J. Chem Soc, Chem Commun 1992, 1361.
13. 1 symmetry likely plays a large role in accepting electron density from the dative THF ligand of solvated imidozirconocene complexes.
14. Lee, S.Y.; Bergman, R.G. J Am Chem Soc 1995, 117, 5877.
15. Lee, S.Y. Ph.D. thesis, University of California, Berkeley, 1995.
16. Schaller, C.P.; Cummins, C.C.; Wolczanski, P.T. J Am Chem Soc 1996, 118, 591.
17. Thompson, M.E.; Baxter, S.M.; Bulls, A.R.; Burger, B.J.; Nolan, M.C.; Santarsiero, B.D.; Schaefer, W.P.; Bercaw, J.E. J Am Chem Soc 1987, 109, 203.
18. Bennett, J.L.; Wolczanski, P.T. J Am Chem Soc 1997, 119, 10696.
19. Quignard, F.; Agnés, C.; Basset, J.-M. J Chem Soc, Chem Commun 1991, 1589.
20. Watson, P.L.; Parshall, G.W. Acc Chem Res. 1985, 18, 51.
21. Fendick, C.M.; Marks, T.J. J Am Chem Soc 1986, 108, 425.
22. Baranger, A.M.; Walsh, P.J.; Bergman, R.G. J Am Chem Soc 1993, 115, 2753.
23. Lee, S.Y.; Bergman, R.G. Tetrahedron 1995, 51, 4255.
24. Hanna, T.A.; Baranger, A.M.; Walsh, P.J.; Bergman, R.G. J Am Chem Soc 1995, 117, 3292.
25. Harlan, C.J.; Tunge, J.A.; Bridgewater, B.M.; Norton, J.R. Organometallics 2000, 19, 2365.
26. Walsh, P.J.; Baranger, A.M.; Bergman, R.G. J Am Chem Soc 1992, 114, 1708.
27. McGrane, P.L.; Livinghouse, T. J Org Chem 1992, 57, 1323.
28. McGrane, P.L.; Jensen, M.; Livinghouse, T. J Am Chem Soc 1992, 114, 5459.
29. Humphries, M.J.; Douthwaite, R.E.; Green, M.L.H. J Chem Soc, Dalton Trans 2000, 2952.
30. Lee, S.Y.; Bergman, R.G. J Am Chem Soc 1996, 118, 6396.
31. Thorman, J.L.; Guzei, I.A.; Young, J.V.G.; Woo, L.K. Inorg Chem 2000, 39, 2344.
32. Blake, A.J.; McInnes, J.M.; Mountford, P.; Nikonov, G.I.; Swallow, D.; Watkin, D.J. J Chem Soc, Dalton Trans 1999, 379.
33. Thorman, J.L.; Guzei, I.A.; Young, J.V.G.; Woo, L.K. Inorg Chem 1999, 38, 3814.
34. Meyer, K.E.; Walsh, P.J.; Bergman, R.G. J Am Chem Soc 1995, 117, 974.
35. Zuckermann, R.L.; Bergman, R.G. Organometallics 2000, 19, 4795.
36. Zuckermann, R.L.; Bergman, R.G. Organometallics 2001, 20, 1792.
37. Meyer, K.E.; Walsh, P.J.; Bergman, R.G. J Am Chem Soc 1994, 116, 2669.
38. Krska, S.W.; Zuckermann, R.L.; Bergman, R.G. J Am Chem Soc 1998, 120, 11828.
39. Cantrell, G.K.; Geib, S.J.; Meyer, T.Y. Organometallics 2000, 19, 3562.
40. The imine metatheses discussed here, as well as an example by Meyer et al. (ref. 37), seem to proceed by straightforward cycloaddition/cycloreversion pathways. However, there have been several recent examples of transition metal "catalyzed" imine metatheses where the kinetic data do not support similar cycloaddition/cycloreversion sequences. See (a) McInnes, J.M.; Mountford, P. J Chem Soc, Chem Commun 1998, 1669.
41. (b) Burland, M.C.; Pontz, T.W.; Meyer, T.M. Organometallics. 2002, 21, 1933.
42. Müller, T.E.; Beller, M. Chem Rev 1998, 98, 675.
43. Johnson, J.S.; Bergman, R.G. J Am Chem Soc 2001, 123, 2329.
44. Straub, B.F.; Bergman, R.G. Angew Chem Intl Ed 2001, 40, 4632.
45. Shi, Y.; Ciszewski, J.T.; Odom, A.L. Organometallics 2001, 20, 3967.
46. Cao, C.; Ciszewski, J.T.; Odom, A.L. Organometallics 2001, 20, 5011.
47. Haak, E.; Bytschkov, I.; Doye, S. Angew Chem Intl Ed 1999, 38, 3389.
48. Pohlki, F.; Doye, S. Angew Chem Intl Ed 2001, 40, 2305.
49. Heutling, A.; Doye, S.J. Org Chem 2002, 67, 1961.
50. Brintzinger, H.H.; Fischer, D.; Müllhaupt, R.; Rieger, B.; Waymouth, R.M. Angew Chem Intl Ed Engl. 1995, 34, 1143.
51. Johannes, C.W.; Visser, M.S.; Weatherhead, G.S.; Hoveyda, A.H. J Am Chem Soc 1998, 120, 8340.
52. Xu, Z.; Johannes, C.W.; Houri, A.F.; La, D.S.; Cogan, D.A.; Hofilena, G.E.; Hoveyda, A.H. J Am Chem Soc 1997, 119, 10302.
53. Hoveyda, A.H.; Morken, J.P. Angew Chem Intl Ed Engl. 1996, 35, 1263.
54. Yun, J.; Buchwald, S.L. J Am Chem Soc 1999, 121, 5640.
55. Verdaguer, X.; Lange, U.E.W.; Reding, M.T.; Buchwald, S.L. J Am Chem Soc 1996, 118, 6784.
56. Jin, J.; Chen, E.Y.-X. Organometallics 2002, 21, 13.