In situ formation of palladium(0) from a P,C-palladacycle

Tetrahedron

Volumn 61, Issue 41, 2005, Pages 9670-9678

  D'Orlyé, Fanny ^a   Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Mechanism, cyclic voltammetry; Palladacycle; Reductive elimination

Indexed keywords

ACETIC ACID; BIS(MU ACETATO)BIS[2 (DI 2 TOLYLPHOSPHINO)BENZYL]DIPALLADIUM; DIMER; HALIDE; MONOMER; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; REDUCING AGENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLIC POTENTIOMETRY; HECK REACTION; HIGH TEMPERATURE PROCEDURES; OXIDATION; PRIORITY JOURNAL; REDUCTION;

EID: 24344488036     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.098     Document Type: Article

References (38)

1. For seminal works, see: (a) W.A. Herrmann, C. Brossmer, K. Ölefe, C.-P. Reisinger, T. Priermeier, M. Beller, and H. Fischer Angew. Chem., Int. Ed. Engl. 34 1995 1844 1848
2. M. Beller, H. Fischer, W.A. Herrmann, K. Ölefe, and C. Brossmer Angew. Chem., Int. Ed. Engl. 34 1995 1848 1849
3. W.A. Herrmann, C. Brossmer, C.-P. Reisinger, T.H. Riermeier, K. Ölefe, and M. Beller Chem. Eur. J. 3 1997 1357 1364
4. For recent reviews, see: (a) W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Organomet. Chem. 576 1999 23 41
5. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 1999 3009 3066
6. J. Dupont, M. Pfeffer, and J. Spencer Eur. J. Inorg. Chem. 2001 1917 1927
7. W.A. Herrmann, K. Ölefe, D.v. Preysing, and S.K. Schneider J. Organomet. Chem. 687 2003 229 248
8. R.B. Bedford J. Chem. Commun. 2003 1787 1796
9. I.P. Beletskaya, and A.V. Cheprakov J. Organomet. Chem. 687 2004 229 248
10. J. Louie, and J.F. Hartwig Angew. Chem., Int. Ed. 35 1996 2359 2361
11. B.L. Shaw New J. Chem. 1998 77 79
12. V.P.W. Böhm, and W.A. Herrmann Chem. Eur. J. 7 2001 4191 4197
13. P. Fitton, J.E. McKeon, and B.C. Ream Chem. Commun. 1969 370 371
14. F. Paul, J. Patt, and J.F. Hartwig J. Am. Chem. Soc. 116 1994 5969 5970
15. F. Paul, J. Patt, and J.F. Hartwig Organometallics 14 1995 3030 3039
16. J.F. Hartwig, and F. Paul J. Am. Chem. Soc. 114 1995 5373 5374
17. 0 complexes, see: (a) K. Nagayama, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 72 1999 799 803
18. R. Kuwano, Y. Kondo, and Y. Matsuyama J. Am. Chem. Soc. 125 2003 12104 12105
19. C. Amatore, A. Jutand, and M.A. M'Barki Organometallics 11 1992 3009 3013
20. C. Amatore, E. Carré, A. Jutand, and M.A. M'Barki Organometallics 14 1995 1818 1826
21. C. Amatore, E. Carré, A. Jutand, M.A. M'Barki, and G. Meyer Organometallics 14 1995 5605 5614
22. C. Amatore, A. Jutand, and A. Thuilliez Organometallics 20 2001 3241 3249
23. 10b This effect is amplified at low scan rates (long times). Consequently, the concentration of the first electroactive species as measured by its reduction (or oxidation) peak current is not the thermodynamic concentration but a higher dynamic concentration.
24. A.J. Bard, and L.R. Faulkner Electrochemical methods 2nd ed. 2001 Wiley New York
25. S.G. Fiddy, J. Evans, M.A. Newton, T. Neisius, R.P. Tooze, and R. Oldman Chem. Commun. 2003 2682 2683
26. For the characterization of cationic palladium complexes in DMF see: A. Jutand Eur. J. Inorg. Chem. 2003 2017 2040
27. 1, which presently is the major one (Fig. 1a). Consequently, the acetate ions should be generated at the same concentration as the cationic complex and their oxidation peak current should be detected, which was not observed (Fig. 1b).
28. For equilibrium between dimers and monomers in DMF, see: C. Amatore, A. Bahsoun, A. Jutand, G. Meyer, A. Ndedi Ntepe, and L. Ricard J. Am. Chem. Soc. 125 2003 4212 4222
29. 0 complex since no reaction occurred after addition of PhI in excess (0.25 mmol) after 4 days.
30. 7b
31. 2 complexes see: (b) C. Amatore, A. Jutand, F. Khalil, M.A. M'Barki, and L. Mottier Organometallics 12 1993 3168 3178
32. and C. Amatore, and A. Jutand Coord. Chem. Rev. 1998 178 180 pp 511-528
33. 9c
34. R. Giovannini, and P. Knochel J. Am. Chem. Soc. 125 1998 11186 11187
35. 20
36. J. Vicente, M.C. Lagunas, E. Bleuel, and M.C. Ramirez de Arellano J. Organomet. Chem. 648 2002 62 71
37. A.J. Cheney, and B.L. Shaw J. Chem. Soc., Dalton Trans. 1972 860 865
38. Y. Takahashi, I. Ito Ts, and Y. Ishii J. Chem. Soc., Chem. Commun. 1970 1065 1070