Evidence for an equilibrium between neutral and cationic arylpalladium(II) complexes in DMF. Mechanism of the reduction of cationic arylpalladium(II) complexes

Acta Chemica Scandinavica

Volumn 52, Issue 1, 1998, Pages 100-106

  Amatore, Christian ^a   Carré, Emmanuelle ^a   Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002493659     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.52-0100     Document Type: Article

References (40)

1. Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press, London 1985.
2. Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry, John Wiley & Sons, Chichester 1995.
3. Malleron, J.-L., Fiaud, J.-C. and Legros, J-Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles, Academic Press, London 1997.
4. Kumada, M. Pure Appl. Chem. 52 (1980) 669.
5. Negishi, E. I. Acc. Chem. Res. 15 (1982) 340.
6. Stille, J. K. Angw. Chem. Int. Ed. Engl. 25 (1986) 508.
7. Heck, R. F. Org. React. 27 (1982) 345.
8. de Mejeire, A. and Meyer, F. E. Angw. Chem. Int. Ed. Engl. 33 (1994) 2379.
9. P. Fitton, M. P. Johnson and J. E. McKeon, J. Chem. Soc., Chem. Commun. (1968) 6.
10. Fitton, P. and Rick, E. A. J. Organomet. Chem. 28 (1971) 287.
11. Coulson, D. R. J. Chem. Soc., Chem. Commun. (1968) 1530.
12. Amatore, C., Jutand, A., Khalil, F., M'Barki, M. A. and L. Mottier Organometallics 12 (1993) 3168.
13. Wallow, T. I., Goodson, F. E. and Novak, B. M. Organometallics 15 (1996) 3708.
14. Herrmann, W. A., Thiel. W. R., Broßmer, C., Öfele, K., Priermeier, T. and Scherer, W. J. Organomet. Chem. 461 (1993) 51.
15. Amatore, C., Carré, E., Jutand, A., M'Barki, M. A. and Meyer, G. Organometallics 14 (1995) 5605.
16. Amatore, C., Jutand, A. and M'Barki, M. A. Organometallics 11 (1992) 3009.
17. Amatore, C., Carré, E., Jutand, A. and M'Barki, M. A. Organometallics 14 (1995) 1818.
18. Ishiyama, T., Murata, M. and Miyaura, N. J. Org. Chem. Soc. 60 (1995) 7508.
19. Jutand, A. and Mosleh, A. Organometallics 14 (1995) 1810.
20. Amatore, C., Jutand, A., Khalil, F. and Nielsen, M. F. J. Am. Chem. Soc. 114 (1992) 7076.
21. Bard, A. J. and Faulkner, L. R. Electrochemical Methods, Wiley, New York 1980, pp. 443-449.
22. Amatore, C., Azzabi, M., Calas, P., Jutand, A., Lefrou, C. and Rollin, Y. J. Electroanal. Chem. 288 (1990) 45.
23. Bard, A. J. and Faulkner, L. R. Electrochemical Methods, Wiley, New York 1980, pp.136-143.
24. 3 as a base, the amount of the cationic complex was less because protons have been partially neutralized.
25. 2. See: Kayaki, Y., Shimizu, I. and Yamamoto, A. Chem. Lett. (1995) 1089 and Ref. 26.
26. Kayaki, Y., Kawataka, F., Shimizu, I. and Yamamoto, A. Chem. Lett. (1994) 2171.
27. 30-33
28. Kawataka, F., Shimizu, I. and Yamamoto, A. Bull. Chem. Soc. Jpn. 68 (1995) 654.
29. Brown, J. M., Pérez-Torrente, J. J., Alcock, N. W. and Clase, H. J. Organometallics 14 (1995) 207.
30. Cabri, W. and Candiani, I. Acc. Chem. Res. 28 (1995) 2.
31. Karabellas, K., Westerlund, C. and Hallberg, A. J. Org. Chem. 50 (1985) 3896.
32. Portnoy, M., BenDavid, Y., Rousso, I. and Milstein, D. Organometallics 13 (1994) 3465.
33. Kraatz, H. B. and Milstein, D. J. Organomet. Chem. 448 (1995) 223.
34. Kawataka, F., Kayaki, Y., Shimizu, I. and Yamamoto, A. Organometallics 13 (1994) 3515.
35. Markies, B. A., Kruis, D., Rietveld, H. P., Verkerk, K. A. N., Boersma, J., Kooijman, H., Lakin, M. T., Spek, A. L. and van Koten, G. J. Am. Chem. Soc. 117 (1995) 5263.
36. Amatore, C. and Savéant, J-M. J. Electroanal. Chem. 125 (1981) 1.
37. Amatore, C. and Savéant, J-M. J. Electroanal. Chem. 86 (1978) 227.
38. Amatore, C. and Pflüger, F. Organometallics 9 (1990) 2276.
39. + is increased, because the backward reaction of eqn. (10) is of second order. Increasing the concentration of the initial cationic complex also results in a shift of the equilibrium (20) to its left-hand side with, as consequences, a smaller production of biphenyl, as observed.
40. Amatore, C. and Jutand, A. Organometallics 7 (1988) 2203.