Rate and mechanism of the oxidative addition of vinyl triflates and halides to palladium(0) complexes in DMF

Organometallics

Volumn 22, Issue 21, 2003, Pages 4229-4237

  Jutand, Anny ^a   Négri, Serge ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BROMINE COMPOUNDS; COMPLEXATION; DECOMPOSITION; HALIDE MINERALS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RATE CONSTANTS; REACTION KINETICS; SALTS; SOLVENTS; STOICHIOMETRY;

BROMIDES; COORDINATING SOLVENT; ELECTROSPRAY MASS SPECTROMETRY; HALIDES; OXIDATIVE ADDITION; PALLADIUM COMPLEXES; VINYL PHOSPHONIUM SALTS; VINYL TRIFLATES;

PALLADIUM COMPOUNDS;

EID: 10744221273     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030298c     Document Type: Article

References (39)

1. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810.
2. Jutand, A.; Mosleh, A. J. Org. Chem. 1997, 62, 261.
3. Jutand, A.; Hii, K. K.; Thornton-Pett, M.; Brown, J. M. Organometallics 1999, 18, 5367.
4. Alcazar-Roman, L. M.; Hartwig, J. F. Organometallics 2002, 21 491.
5. For seminal works see: (a) Cacchi S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 2271.
6. (b) Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821.
7. (c) Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
8. (d) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
9. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
10. (f) Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47.
11. (g) Ritter, K. Synthesis 1993, 735.
12. (a) Jutand, A.; Négri, S. Synlett 1997, 719.
13. (b) Jutand, A.; Négri, S. Eur. J. Org. Chem. 1998, 1811.
14. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
15. (a) Kowalski, M. H.; Stang, P. Organometallics 1986, 5, 2392.
16. (b) Stang, P. J.; Kowalski, M. H.; Schiavelli, M. D.; Longford, D. J. Am. Chem. Soc. 1989, 111, 3347.
17. Brown, J. M.; Cooley, N. A. J. Chem. Soc., Chem. Commun. 1988, 1345.
18. Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1981, 209, 109.
19. Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670.
20. For the characterization of ionic coordination compounds by conductivity measurements see: Geary, W. J. Coord. Chem. Rew. 1971, 7, 81.
21. For the use of conductivity measurements for the characterization of cationic organopalladium(II) complexes and the determination of kinetic data see: Jutland, A. Eur. J. Inorg. Chem. 2003, 2017.
22. For a related vinylphosphonium salt see ref 16.
23. Amatore, C.; Khalil, F.; Jutand, A.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
24. (a) Kowalski, M. H.; Hinkle, R. J.; Stang, P. J. J. Org. Chem. 1989, 54, 2783.
25. (b) Hinkle, R. J.; Stang, P. J.; Kowalski, M. H. J. Org. Chem. 1990, 55, 5033.
26. (a) Mann, B.E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667.
27. (b) Loar, M. K.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4174.
28. 2 observed in related oxidative addition of vinyl bromides.
29. Fauvarque, J. F.; Pflüger, F.; Troupel, M. J. Organomet. Chem. 1981, 209, 109.
30. x). (b) See ref 20a for the expression of the rate law with X - OTFf.
31. 0 at the end of the oxidative addition.
32. 0 complex to aryl halides before the oxidative addition step has been discussed in detail by Alcazar-Roman and Hartwig.
33. Rosevear, D. T.; Stone, F. G. J. Chem. Soc. A 1968, 164.
34. Stang, P. J.; Hanack, M.; Subramanian, L. Synthesis 1982, 85.
35. (b) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
36. (c) Pal, K. Synthesis 1995, 1485.
37. Summerville, R. H.; Senkler, C. A.; Schleyer, P. v. R.; Dueber, T. E.; Stang, P. J. J. Am. Chem. Soc. 1974, 96, 1100.
38. Willems, A. G. M.; Pandit, U. K.; Huisman, H. O. Recl. Trav. Chim. Pays-Bas 1965, 84, 389.
39. Cristol, S. J.; Norris, W. P. J. Am. Chem. Soc. 1953, 75, 2645.