Structural and kinetic effects of chloride ions in the palladium-catalyzed allylic substitutions

Journal of Organometallic Chemistry

Volumn 687, Issue 2, 2003, Pages 365-376

  Cantat, Thibault ^a   Génin, Emilie ^a   Giroud, Claire ^a   Meyer, Gilbert ^a   Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Allyl complex; Allylic substitution; Chloride ions; Kinetics; Mechanism; Palladium

Indexed keywords

BUTANE; CHLORIDE ION; FERROCENE DERIVATIVE; LIGAND; MORPHOLINE; PALLADIUM COMPLEX;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; REACTION TIME; SUBSTITUTION REACTION;

GOES;

EID: 0345306222     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00791-5     Document Type: Article

References (42)

1. Tsuji J. Palladium Reagents and Catalysts 1996 290 John Wiley & Sons Chichester
2. Godleski S.A. in: Trost B.M. Flemming I. Comprehensive Organic Synthesis 4 1991 Pergamon Oxford
3. Frost C.G. Howard J. Williams J.M.J. Tetrahedron: Asymmetry 3 1992 1089
4. Consiglio G. Waymouth R. Chem. Rev. 89 1989 257
5. Pfaltz A. Acc. Chem. Rev. 26 1993 339-345
6. Hayashi T. in: Ojima I. Catalytic Asymmetric Synthesis 1993 325 VCH New York
7. Trost B.M. Van Vranken D.L. Chem. Rev. 96 1996 395
8. Trost B.M. Acc. Chem. Res. 29 1996 355
9. E.I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, 2002, vol. 2, Wiley Interscience, New York, pp. 1663-2027.
10. Amatore C. Jutand A. Meyer G. Mottier L. Chem. Eur. J. 5 1999 466
11. Amatore C. Gamez S. Jutand A. Chem. Eur. J. 7 2001 1273
12. Amatore C. Gamez S. Jutand A. Meyer G. Mottier L. Electrochim. Acta 46 2001 3237
13. Amatore C. Jutand A. M'Barki M.A. Meyer G. Mottier L. Eur. J. Inorg. Chem. 2001 873
14. Powell J. Shaw B.L. J. Chem. Soc. A 1967 1839
15. Braunstein P. Naud F. Dedieu A. Rohmer M.-M. DeCian A. Rettig S.J. Organometallics 20 2001 2966
16. Kollmar M. Helmchen G. Organometallics 21 2002 4771
17. Malaisé G. Barloy L. Osborn J.A. Kyritsakas N. C. R. Chimie 5 2002 289
18. Akermark B. Akermark G. Hegedus L.S. Zetterberg K. J. Am. Chem. Soc. 103 1981 2037
19. Bäckvall J.E. Nordberg R.E. J. Am. Chem. Soc. 103 1981 4959
20. Nordberg R.E. Bäckvall J.E. J. Organomet. Chem. 285 1985 C24
21. Kawatsura M. Uozumi Y. Hayashi T.J. Chem. Soc. Chem. Commun. 1998 217
22. Lloyd-Jones G.C. Stephen S.C. J. Chem. Soc. Chem. Commun. 1998 2321
23. Lloyd-Jones G.C. Stephen S.C. Chem. Eur. J. 4 1998 2539
24. Trost B.M. Toste F.D. J. Am. Chem. Soc. 121 1999 4545
25. 3P led to a complex mixture
26. 3, dioxygen) [3]
27. II complexes by conductivity measurements in DMF, see: Jutand A. Eur. J. Inorg. Chem. 2003 2017
28. -1) [2a].
29. Jutand A. Mosleh A. Organometallics 14 1995 1810
30. -1. This might be due to the formation of a small amount of an allyl-phosphonium salt [14].
31. -1) [2a]
32. Powell J. Shaw B.L. J. Chem. Soc. A 1968 774
33. Hayashi T. Yamamoto A. Hagihara T. J. Org. Chem. 51 1986 723
34. Baboulène M. Torregrosa J.L. Spéziale V. Lattes A. Bull. Soc. Chim. Fr. 11-12 1980 565
35. The kinetics was monitored at -25 °C. Monitoring the kinetics by cyclic voltammetry at such a low temperature was thus a problem due to the high resistivity of the solution.
36. Kuhn O. Mayr H. Angew. Chem. Int. Ed. 38 1999 343
37. 0 at 296 nm.
38. 0t+1.
39. N2′ substitution of morpholine on allyl bromide see: Butler G. Bunch R.L. J. Am. Chem. Soc. 71 1949 3120
40. For a review on the halide effects in transition metal catalysis, see: Fagnou K. Lautens M. Angew. Chem. Int. Ed. 41 2002 26
41. Takahashi Y. Ito Ts. Sakai S. Ishii Y. J. Chem. Soc. Chem. Commun. 1970 1065
42. Auburn P.M. Mackenzie P.B. Bosnish B. J. Am. Chem. Soc. 107 1985 2033