The palladium-catalyzed carbonylation of nitrobenzene into phenyl isocyanate: The structural characterization of a metallacylic intermediate

Organometallics

Volumn 17, Issue 11, 1998, Pages 2199-2206

  Paul, Frédéric ^a   Fischer, Jean ^a   Ochsenbein, Philippe ^a   Osborn, John A ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001321504     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9708485     Document Type: Article

References (47)

1. (a) Cenini, S.; Ragaini, F. In Reductive Carbonylation of Organic Nitroaromatic Compounds; Kluwer Acad. Publishers: Dordrecht, The Netherlands, 1997.
2. (b) Drent, E. Pure Appl. Chem. 1990, 62, 661.
3. (c) Cenini, S.; Crotti, C. In Catalysis by Metal Complexes; Noëls, A. F., Graziani, M., Hubert, A. J., Eds.; Kluwer Acad. Publishers: Dordrecht, The Netherlands, 1997; Vol. 112, p 311.
4. (d) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; J. Wiley & Sons: New York, 1992.
5. (e) Ragaini, F.; Cenini, S.; J. Mol. Catal. A: Chem. 1996, 109, 1.
6. (a) Kunin, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1989, 111, 2739.
7. (b) Gargulak, J. D.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1991, 113, 1054.
8. (c) Sherlock, S. J.; Boyd, D. C.; Moasser, B.; Gladfelter, W. L. Inorg. Chem. 1991, 30, 3626.
9. (d) Gargulak, J. D.; Berry, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1992, 114, 8933.
10. (e) Gargulak, J. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1994, 116, 3792.
11. (f) Skoog, S. J.; Campbell, J. P.; Gladfelter, W. L. Organometallics 1994, 13, 4137.
12. Cenini, S.; Crotti, C.; Pizzotti, M.; Porta, F. J. Org. Chem. 1988, 53, 1243.
13. (a) Ragaini, F.; Cenini, S.; Fumagalli, A.; Crotti, C. J. Organomet. Chem. 1992, 401.
14. (b) Ragaini, F.; Cenini, S. Organometallics 1994, 13, 1178.
15. (a) Alessio, E.; Mestroni, G. J. Mol. Catal. 1984, 26, 337.
16. (b) Alessio, E.; Mestroni, G. J. Organomet. Chem. 1985, 291, 117.
17. (c) Cennini, S.; Ragaini, F.; Pizzotti, M.; Porta, F.; Mestroni, G.; Alessio, E. J. Mol. Catal. 1991, 64, 179.
18. (a) Wehman, P.; Dol, G. C.; Moorman, E.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1994, 13, 4856.
19. (b) Wehman, P.; Kaasjager, V. E.; de Lange, W. G. J.; Hartl, F.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3751.
20. (c) Wehman, P.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Commun. 1996, 217.
21. (d) Wehman, P.; Borst, L.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Mol. Catal. A: Chem. 1996, 112, 23.
22. (e) Wehman, P.; Borst, L.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Ber./Recl. 1997, 130, 13.
23. (a) Drent, E.; van Leeuwen, P. W. N. M. Eur. Pat. Appl. EP 86281, 1981.
24. (b) Alessio, E.; Mestroni, G. Italian Patent 21401A84, 1984.
25. (c) Alessio, E.; Mestroni, G. EP 0169650 A2, 1985.
26. (d) Drent, E. Eur. Pat. Appl. EP 224292, 1986.
27. (e) Drent, E. Eur. Pat. Appl. EP 231045 1987.
28. Leconte, P.; Metz, F.; Mortreux, A.; Osborn, J. A.; Paul, F.; Petit, F.; Pillot, A. J. Chem. Soc., Chem. Commun. 1990, 1616.
29. Paul, F.; Fischer, J.; Ochsenbein, P.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1638.
30. Paul, F.; Fischer, J.; Ochsenbein, P.; Osborn, J. A. To be submitted.
31. Paul, F. Thesis, Louis Pasteur/Strasbourg (I), 1993.
32. Cenini, S.; Porta, F.; Pizzotti, M.; Crotti, C. J. Chem. Soc., Dalton Trans. 1985, 163.
33. Dahlenburg, L.; Prengel, C. Inorg. Chim. Acta 1986, 122, 55.
34. Pizzotti, M.; Porta, F.; Cenini, S.; Demartin, F.; Masciocchi, N. J. Organomet. Chem. 1987, 330, 265.
35. Glueck, D. S.; Wu, J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 2041.
36. For another proposed mechanism involving only metallacycles in rhodium-catalyzed reactions, see: (a) Unverfehrt, K.; Schwetlick, K. React. Kinet. Catal. Lett. 1977, 6, 231.
37. (b) Unverfehrt, K.; Höntsch, R.; Schwetlick, K. J. Prakt. Chem. 1979, 321, 86.
38. (c) Unverfehrt, K.; Höntsch, R.; Schwetlick, K. J. Prakt. Chem. 1979, 321, 928.
39. Chetcuti, P. A.; Walker, J. A.; Knobler, K. B.; Hawthorne, M. F. Organometallics 1988, 7, 641.
40. Werner, H.; Brekau, U.; Nurnberg, O.; Zeier, B. J. Organomet. Chem. 1992, 440, 389.
41. Herskovitz, T.; Guggenberger, L. J. J. Am. Chem. Soc. 1976, 98, 1615.
42. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
43. Belser, P.; von Zelewsky, A. Helv. Chim. Acta 1980, 63, 1675.
44. McKeon, J. E.; Fitton, P. Tetrahedron 1972, 28, 233.
45. Ryan, D. E. Can. J. Res., Part B 1949, 27, 938.
46. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
47. Frenz, B. A. The ENRAF-Nonius CAD4-SDP In Computing Crystallography; Olthof-Hazekampf, R., Schenk, H., van Koningveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, The Netherlands, 1978; pp 64-71.