Mechanism of the alkoxycarbonylation of alkynes in the presence of the Pd(OAc)2/PPh2PY/CH3SO3H catalytic system

Organometallics

Volumn 17, Issue 4, 1998, Pages 630-635

  Scrivanti, Alberto ^a   Beghetto, Valentina ^a   Campagna, Eleonora ^a   Zanato, Monica ^a   Matteoli, Ugo ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001426101     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9705968     Document Type: Article

References (47)

1. (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1996; p 471.
2. (b) Bates, R. W. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 3, p 349.
3. (c) Colquhoun, H. M.; Thomson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991.
4. (d) Bird, C. W. Chem. Rev. 1962, 62, 283.
5. (a) Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247.
6. (b) Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1994, 475, 57.
7. Doyle, M. J.; van Gogh, J.; van Ravenswaay Claasen, J. Eur. Pat. Appl. EP-A-392,601, 1990; Chem. Abstr. 1991, 114, 102997p.
8. Scrivanti, A.; Matteoli, U. Tetrahedron Lett. 1995, 36, 9015.
9. Matteoli, U.; Scrivanti, A. Unpublished results.
10. Milstein, D. Acc. Chem. Res. 1988, 21, 428.
11. The chemistry of metal alkoxides has been reviewed: Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
12. Murray, T. F.; Norton, J. R. J. Am. Chem. Soc. 1979, 101, 4107.
13. Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505.
14. Two recent reviews on the chemistry of the Pd-H moiety: (a) Takacs, J. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 3, p 46. (b) Grushin, V. V. Chem. Rev. 1996, 96, 2011.
15. Two recent reviews on the chemistry of the Pd-H moiety: (a) Takacs, J. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 3, p 46. (b) Grushin, V. V. Chem. Rev. 1996, 96, 2011.
16. (a) Zargarian, D.; Alper, H. Organometallics 1993, 12, 712.
17. (b) Tsuji, J. Acc. Chem. Res. 1969, 2, 144.
18. Lewandos, G. S.; Maki, J. W.; Ginnebaugh, J. P. Organometallics 1982, 1, 1700.
19. Clark, H. C.; Milne, C. R. J. Organomet. Chem. 1978, 161, 51.
20. Portnoy, M.; Milstein, D. Organometallics 1994, 13, 600.
21. Reger, D. L.; Garza, D. G. Organometallics 1993, 12, 554.
22. Newkome, G. R. Chem. Rev. 1993, 93, 2067 and references therein.
23. Lewandos in ref 12 proposed the reversible formation of a vinyl species to account for the H/D exchange observed to occur with 1-alkynes in the presence of silver triflate.
24. Trost B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301.
25. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774.
26. Mullen, A. In New Syntheses with Carbon Monoxide; Falbe, J., Ed.; Springer Verlag: New York, 1980; Chapter 3, and references therein.
27. D = 1.38 at 323 K.
28. For a concerted mechanism a low kinetic deuterium isotope effect is expected: Nakamura, A.; Otsuka, S. J. Mol. Catal. 1976, 1, 285
29. Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177.
30. Amatore, C.; Carrè, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818.
31. Krause, J.; Bonrath, W.; Pörschke, K. R. Organometallics 1992, 11, 1158.
32. Henderson, R. A.; Lowe, D. J.; Salisbury, P. J. Organomet. Chem. 1995, 489, C22.
33. (a) Barlex, D. M.; Kemmitt, R. D. W.; Littlecott, G. W. J. Chem. Soc., Chem. Commun. 1969, 613.
34. (b) Tripathy, P. B.; Roundhill, D. M. J. Am. Chem. Soc. 1970, 92, 3825.
35. (c) Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667.
36. (d) Bennett, M. A.; Rokicki, A. Aust. J. Chem. 1985, 38, 1307.
37. Westheimer, F. W. Chem. Rev. 1961, 61, 265.
38. Laidler, K. J. Chemical Kinetics; Harper & Row: New York, 1987; Chapter 11.
39. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 747.
40. Schmid, G. H. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; Part 1, Chapter 8.
41. Allen, A. D.; Chiang, Y.; Kresge, A. J.; Tidwell, T. T. J. Org. Chem. 1982, 47, 775.
42. Milstein, D. J. Chem. Soc., Chem. Commun. 1986, 817.
43. Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, Y. Organometallics 1987, 6, 1640.
44. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, U.K., 1996.
45. Stephenson, T. A.; Morehouse, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. A 1965, 3632.
46. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
47. Barder, T. J.; Cotton, F. A.; Powell, G. L.; Tetrick, S. M.; Walton, R. A. J. Am. Chem. Soc. 1984, 706, 1323.