Rate and mechanism of the reversible formation of cationic (η3-allyl)-palladium complexes in the oxidative addition of allylic acetate to palladium(0) complexes ligated by diphosphanes

Chemistry - A European Journal

Volumn 7, Issue 6, 2001, Pages 1273-1280

  Amatore, Christian ^a   Gamez, Sophie ^a   Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Allyl complexes; Kinetics; Oxidative addition; P,P ligands; Palladium

Indexed keywords

IONIZATION; OXIDATION; PALLADIUM COMPOUNDS; POSITIVE IONS; REACTION KINETICS; ULTRAVIOLET SPECTROSCOPY;

LIGANDS;

COMPLEXATION;

1,1' BIS(DIPHENYLPHOSPHANYL)FERROCENE; 1,4 BIS(DIPHENYLPHOSPHANYL)BUTANE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONDUCTANCE; EQUILIBRIUM CONSTANT; ULTRAVIOLET SPECTROSCOPY;

EID: 0035896231     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010316)7:6<1273::AID-CHEM1273>3.0.CO;2-7     Document Type: Article

References (25)

1. a) P. R. Auburn, P. B. Mackenzie, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2033-2046;
2. b) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054;
3. c) J. Tsuji, Tetrahedron 1986, 42, 4361-4401;
4. d) G. Consiglio, R. Waymouth, Chem. Rev. 1989, 89, 257-273;
5. e) S. A. Godleski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Flemming), Pergamon, Oxford, 1991;
6. f) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122;
7. g) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345;
8. h) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995, p. 290;
9. i) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364;
10. j) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
11. C. Amatore, A. Jutand, G. Meyer, L. Mottier, Chem. Eur. J. 1999, 5, 466-473.
12. a) M. Moreno-Mañas, L. Morral, R. Pleixats, J. Org. Chem. 1998, 65, 6160-6166;
13. b) C. Amatore, S. Gamez, A. Jutand, G. Meyer, M. Moreno-Mañas, L. Morral, R. Pleixats, Chem. Eur. J. 2000, 6, 3372-3376.
14. 2] with bidentate diphosphane ligands in allylic substitutions see: J. C. Fiaud, A. Hibon de Gournay, M. Larchevêque, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185.
15. C. Amatore, G. Broeker, A. Jutand, F. Khalil, J. Am. Chem. Soc. 1997, 119, 5176-5185.
16. a) J. C. Fiaud, J. Y. Legros, unpublished results;
17. b) J. Y. Legros, Ph.D. Thesis, University Paris XII, Orsay, 1988.
18. 0(dppf)] complexes see:a) J. M. Brown, N. A. Cooley, J. Chem. Soc. Chem. Commun. 1988, 1345-1347;
19. b) A. Jutand, K. K. Hii, M. Thornton-Pett, J. M. Brown, Organometallics 1999, 18, 5367-5374.
20. a) C. Amatore, A. Jutand, F. Khalil, M. A. M'Barki, L. Mottier, Organometallics 1993, 12, 3168-3178;
21. b) C. Amatore, A. Jutand, G. Meyer, Inorg. Chim. Acta. 1998, 273, 76-84.
22. [7a]
23. 0(dppf)] complex (alkene = methylacrylate) see: A. Jutand, K. K. Hii, M. Thornton-Pett, J. M. Brown, Organometallics 1999, 18, 5367-5374.
24. Y. Takahashi, T. Ito, S. Sakai, Y. Ishii, J. Chem. Soc. Chem. Commun. 1970, 1065-1066.
25. J. Powell, B. L. Shaw, J. Chem. Soc. (A) 1968, 774-777.