Copper(II) complexes of novel 1,5-diaza-cis-decalin diamine ligands: An investigation of structure and reactivity

Organometallics

Volumn 21, Issue 21, 2002, Pages 4513-4522

  Kozlowski, Marisa C ^a   Li, Xiaolin ^a   Carroll, Patrick J ^a   Xu, Zhenrong ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTION;

ALCOHOLS; CATALYSTS; CRYSTAL STRUCTURE; DIMERS; SUBSTITUTION REACTIONS;

COMPLEXATION;

EID: 0037625223     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020425p     Document Type: Article

References (40)

1. For reviews, see: (a) Solomon, E. I.; Chen, P.; Metz, M.; Lee, S.-K.; Palmer, A. E. Angew. Chem., Int. Ed. 2001, 40, 4570-4590.
2. (b) Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2605.
3. (c) Klinman, J. P. Chem. Rev. 1996, 96, 2541-2561.
4. (d) Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737-757.
5. For some examples, see: (a) DuBois, J. L.; Mukherjee, P.; Stack, T. D. P.; Hedman, B.; Solomon, E. I.; Hodgson, K. O. J. Am. Chem. Soc. 2000, 122, 5775-5787.
6. (b) Henson, M. J.; Mukheijee, P.; Root, D. E.; Stack, T. D. P.; Solomon, E. I. J. Am. Chem. Soc. 1899, 121, 10332-10345.
7. (c) Root, D. E.; Henson, M. J.; Machonkin, T.; Mukherjee, P.; Stack, T. D. P.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 4982-4990.
8. (d) Mahadevan, V.; Hou, Z.; Cole, A. P.; Root, D. E.; Lal, T. K.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 119, 11996-11997.
9. (e) DuBois, J. L.; Mukherjee, P.; Collier, A. M.; Mayer, J. M.; Solomon, E. I.; Hedman, B.; Stack, T. D. P.; Hodgson, K. O. J. Am. Chem. Soc. 1997, 119, 8578-8579.
10. (f) Cole, A. P.; Root, D. E.; Mukherjee, P.; Solomon, E. I.; Stack, T. D. P. Science 1996, 273, 1848-1850.
11. Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137-1140.
12. Ganguly, B.; Freed, D. A.; Kozlowski, M. C. J. Org. Chem. 2001, 66, 1103-1108.
13. Hathaway, B. J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, N. A., Eds.; Pergamon Press: Oxford, 1987; Chapter 53.
14. Kodera, M.; Tachi, Y.; Kita, T.; Kobushi, H.; Sumi, Y.; Kano, K.; Shiro, M.; Koikawa, M.; Tokii, T.; Ohba, M.; Okawa, H. Inorg. Chem. 2000, 39, 226-234, and references therein.
15. For examples see: (a) Klaassen, M.; Klüfers, P. Z. Anorg. Allg. Chem. 1993, 619, 661-668.
16. (b) Wang, S.; Pang, Z.; Smith, K. D. L.; Wagner, M. L. J. Chem. Soc., Dalton Trans. 1994, 955-964.
17. (c) Klüfers, P.; Piotrowski, H.; Schuhmacher, J. Z. Anorg. Allg. Chem. 1997, 623, 191-199.
18. Crawford, V. H.; Richardson, H. W.; Wasson, J. R.; Hodgson, D. J.; Hatfield, W. E. Inorg. Chem. 1976, 15, 2107-2110.
19. Tsiamis, C. Inorg, Chim. Acta 1992, 198-200, 651-661.
20. Arcus, C.; Fivizzani, K. P.; Pavkovic, S. F. J. Inorg. Nucl. Chem. 1977, 39, 285-287.
21. Funahashi, Y.; Nakaya, K.; Hirota, S.; Yamauchi, O. Chem. Lett. 2000, 1172-1173.
22. Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-L.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271.
23. (a) Childers, L. S.; Folting, K.; Merritt, L. L., Jr.; Streib, W. E. Acta Cryatallogr. B 1975, 31, 924.
24. (b) Lopez, S.; Muravyov, I.; Pulley, S. R.; Keller, S. W. Acta Crystallogr. 1998, C54, 355-357.
25. 2 complexes of sparteine (Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 723, 7475-7476) with 1 and 2 (Kozlowski, M. C.; Li, X. Unpublished results).
26. 2 complexes of sparteine (Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 723, 7475-7476) with 1 and 2 (Kozlowski, M. C.; Li, X. Unpublished results).
27. Hatfield, W. E.; Piper, T. S.; Klabunde, U. Inorg. Chem. 1963, 2, 629-632.
28. (a) Kagan, H. B. Synlett 2001, 888-899.
29. (b) Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402-411.
30. (c) Detlef, H.; Hans-Joachim, D.; Fisher, C.; Buschmann, H.; Baumann, W.; Heller, B. Angew. Chem., Int. Ed. 2000, 39, 495-499.
31. (d) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959.
32. PMS(tm) semiempirical calculations with SPARTAN v5.0 (Wave-function, Inc.: 18401 Von Karman Avenue, Suite 370; Irvine, CA 92612.
33. A crystal structure of the trimer that was generated from the racemic ligand has also been obtained.
34. Models indicate that the heterotrimers also have disfavorable steric interactions due to the close proximity between each of the diamine ligands.
35. The second attacking substrate may also coordinate the copper catalyst or undergo hydrogen bonding with the copper diamine NH groups.
36. (a) bioteX, A suite of Programs for the Collection, Reduction and Interpretation of Imaging Plate Data; Molecular Structure Corporation, 1995.
37. (b) CrystalClear, Rigaku Corporation, 1999.
38. teXsan, Crystal Structure Analysis Package; Molecular Structure Corporation, 1985 and 1992.
39. SIR92. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A.; Polidoro, G. J. Appl. Crystallogr. 1994, 27, 435.
40. Sheldrick, G. M. SHELXL-93, Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1993.