Kinetic studies of acetate exchange in trans-4-acetoxy-[η3-(1,2,3)-cyclohexenyl]palladium complexes. Relevance for asymmetric 1,4-oxidation reactions

Organometallics

Volumn 21, Issue 16, 2002, Pages 3367-3375

  Cotton, Hanna K ^a   Verboom, Renzo C ^a   Johansson, Lars ^a   Plietker, Bernd J ^a,b   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACIDITY; DECOMPOSITION; ISOMERS; LITHIUM COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PALLADIUM COMPOUNDS; REACTION KINETICS; SOLUTIONS; STOICHIOMETRY;

FIRST-ORDER KINETICS;

ORGANOMETALLICS;

EID: 0038575489     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020228q     Document Type: Article

References (42)

1. Bäckvall, J.-E. Palladium-Catalyzed 1,4-Additions to Conjugated Dienes. Review In Metal-catalyzed Cross Coupling Reactions; Stang, P., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1998; pp 339-385.
2. (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, P.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463.
3. (b) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.
4. (c) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474
5. (d) Hamed, O.; Henry, P. M. Organometallics 1998, 17, 5184.
6. (e) Hollis, T. K.; Overman, L. E. J. Organomet. Chem. 1999, 576, 290.
7. (f) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
8. (g) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907.
9. (h) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475.
10. (i) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
11. Bäckvall, J.-E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
12. Bäckvall, J.-E.; Vågberg, J.; Nordberg, R. E. Tetrahedron Lett. 1984, 25, 2717.
13. Bäckvall, J.-E.; Hopkins, R. B.; Grennberg, H.; Mader, M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160.
14. Thorarensen, A.; Palmgren, A.; Itami, K.; Bäckvall, J.-E. Tetrahedron Lett. 1997, 38, 8541.
15. Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.
16. (a) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
17. (b) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475.
18. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447.
19. Seeman, J. I. Chem. Rev. 1983, 83, 83.
20. (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 3543.
21. (b) Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. J. Am. Chem. Soc. 2000, 122, 5968.
22. (a) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, UK, 2000.
23. (b) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Sausalito, 1999.
24. Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779.
25. The regiochemistry can be explained by the proposed mechanisms for 1,4-acetoxychlorination and acyloxyalkoxylation reactions; see also refs 15 and 18.
26. Bäckvall, J.-E.; Granberg, K. L.; Andersson, P. G.; Gatti, R.; Gogoll, A. J. Org. Chem. 1993, 55, 5445.
27. Bäckvall, J.-E.; Nyström, J.-E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676.
28. Kurosawa, H.; Ogoshi, S.; Kawasaki, Y.; Murai, S.; Migoshi, M.; Ikeda, I. J. Am. Chem. Soc. 1990, 112, 2813.
29. Bäckvall, J.-E.; Vågberg, J. O. J. Org. Chem. 1988, 53, 5695.
30. Hupe, E.; Itami, K.; Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. Tetrahedron 1998, 54, 5375.
31. obs were obtained, both with and without the internal standard, for the acetate exchange reaction of substrate 1b.
32. The positive charge at C-4 developed when the acetoxy group is leaving would be stabilized by a butyl or phenyl substituent at C-2. The stabilizing effect is evident from the σ,π resonance form.
33. Thorarensen, A. Unpublished results from these laboratories.
34. (a) Andersen, K. K. Tetrahedron Lett. 1962, 93.
35. (b) Andersen, K. K. J. Org. Chem. 1964, 29, 1953.
36. (c) Carreño, M. C.; Garcia Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003.
37. Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. J. Org. Chem. 1991, 56, 5808.
38. Karlström, A. S. E.; Itami, I.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 1745.
39. Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc., Chem. Commun. 1970, 1065.
40. Kharasch, M. S.; Seyler, R. C.; Mayo, F. R. J. Am. Chem. Soc. 1938, 60, 882.
41. Bökman, F.; Gogoll, A.; Petterson, L. G. M.; Bohman, O.; Siegbahn, H. O. G. Organometallics 1992, 11, 1784.
42. 3 was prepared by a method for purification of nondeuterated silver acetate described by: Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: Oxford, UK, 1980; p 520.