The carbonylation reaction of nitrobenzene to methyl phenylcarbamate: Highly efficient promoters for the palladium-phenanthroline catalytic system based on phosphorus acids

Angewandte Chemie - International Edition

Volumn 42, Issue 25, 2003, Pages 2886-2889

  Ragaini, Fabio ^a   Cognolato, Carlo ^a   Gasperini, Michela ^a   Cenini, Sergio ^a  

^a CNR   (Italy)

Author keywords

Carbamates; Carbonylation; Homogeneous catalysis; Nitroarenes; Palladium

Indexed keywords

CARBONYLATION; CATALYSIS; PALLADIUM; PHOSPHORUS COMPOUNDS;

CATALYTIC SYSTEMS;

BENZENE;

CARBAMIC ACID DERIVATIVE; CARBANILIC ACID METHYL ESTER; NITROBENZENE DERIVATIVE; PALLADIUM; PHENANTHROLINE DERIVATIVE; PHOSPHORUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0037696954     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351004     Document Type: Article

References (32)

1. S. Cenini, F. Regaini, Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Press, Dordrecht, 1997, and references therein.
2. F. Paul, Coord. Chem. Rev. 2000, 20, 269-323, and references therein.
3. A. M. Tafesh, J. Weiguny, Chem. Rev. 1996, 96, 2035-2052, and references therein.
4. E. Drent, P. W. N. M. Van Leeuwen, US 4,474,978, 1984 (Eur. Pat. Appl. EP 86,281, 1983
5. Eur. Pat. Appl. EP 86,281, 1983
6. Chem. Abstr. 1984 100 6109x
7. E. Drent, Eur. Pat. Appl. EP 231,045, 1987
8. Chem. Abstr. 1988 109 128605n
9. A. Bontempi, E. Alessio, G. Chanos, G. Mestroni, J. Mol. Catal. 1987, 42, 67-80.
10. E. Alessio, G. Mestroni, J. Organomet. Chem. 1985, 291, 117-127.
11. S. Cenini, F. Ragaini, M. Pizzotti, F. Porta, G. Mestroni, E. Alessio, J. Mol. Catal. 1991, 64, 179-190.
12. P. Leconte, F. Metz, Eur. Pat. Appl. EP 330,591, 1989
13. Chem. Abstr. 1990 112 78160c
14. P. Wehman, G. C. Dol, E. R. Moorman, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Fraanje, K. Goubitz, Organometallics 1994, 13, 4856-4869.
15. P. Wehman, V. E. Kaasjager, W. G. J. de Lange, F. Hartl, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Fraanje, K. Goubitz, Organometallics 1995, 14, 3751-3761.
16. P. Wehman, L. Borst, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Mol. Catal. A 1996, 112, 23-36.
17. P. Wehman, L. Borst, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Ber. 1997, 130, 13-21.
18. P. Wehman, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Commun. 1996, 217-218.
19. F. Ragaini, S. Cenini, J. Mol. Catal. A 1996, 109, 1-25, and references therein.
20. R. Santi, A. M. Romano, P. Panella, G. Mestroni, It. Pat. Appl. MI96A 002071, 1996.
21. R. Santi, A. M. Romano, P. Panella, G. Mestroni, It. Pat. Appl. MI96A 002072, 1996.
22. R. Santi, A. M. Romano, R. Garrone, P. Panella, It. Pat. Appl. MI97A 000433, 1997.
23. R. Santi, A. M. Romano, P. Panella, C. Santini, J. Mol. Catal. A 1997, 127, 95-99.
24. R. Santi, A. M. Romano, P. Panella, G. Mestroni, A. Sessanta O Santi, J. Mol. Catal. A 1999, 144, 41-45.
25. L. M. Litvinenko, N. M. Oleinik, Russ. Chem. Rev. 1978, 47, 401-415;
26. Usp. Khim. 1978 47, 777-803
27. F. Ragaini, E. Gallo, S. Cenini, J. Organomet. Chem. 2000, 593-594, 109-118.
28. A. P. Kozlov, S. S. Sazhnev, G. A. Kozlova, Yu. S. Andreiichikov, Russ. J. Org. Chem. 1996, 32, 1523-1528;
29. Zh Org Khim 1996 32 1573-1578
30. G. V. Semenyuk, N. G. Razumova, J. Org. Chem. USSR 1986, 22, 996-997; Zh. Org. Khim. 1986, 22, 1109-1110.
31. Zh. Org. Khim. 1986 22, 1109-1110
32. The absolute amounts of all the other reagents (including phen and phosphoric acid) have been kept constant and equal to those reported in Table 1, except for the CO pressure (100 bar). Nitrobenzene conversion was complete in this experiment; thus even higher TONs should be possible.