Carbonylation of dinitrotoluene to dimethyl toluenedicarbamate; high efficiency of phosphorus acids as promoters for the palladium-phenanthroline catalytic system

Advanced Synthesis and Catalysis

Volumn 347, Issue 1, 2005, Pages 105-120

  Gasperini, Michela ^a   Ragaini, Fabio ^a   Cazzaniga, Chiara ^a   Cenini, Sergio ^a  

^a CNR   (Italy)

Author keywords

Carbamates; Carbonylation; Catalysis; Homogeneous; Nitroarenes; Palladium

Indexed keywords

2,2 DIMETHOXYPROPANE; 2,4 DINITROTOLUENE; 2,4 TOLUENEDICARBAMATE; 2,6 DINITROTOLUENE; 4 TOLYLPHOSPHONIC ACID; ACID; AMINE; CARBAMIC ACID DERIVATIVE; DESICCANT; DIMETHYLTOLUENEDICARBAMATE; DINITROARENE; DINITROTOLUENE; METAL COMPLEX; PALLADIUM; PHENANTHROLINE; PHENYLPHOSPHONIC ACID; PHOSPHORUS ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; COOLING; EXPERIMENT; PRECIPITATION; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SOLUBILITY; SYNTHESIS;

EID: 14644416510     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404151     Document Type: Article

References (65)

1. S. Cenini, F. Ragaini, Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Press, Dordrecht, 1997, and references cited therein.
2. F. Paul, Coord. Chem. Rev. 2000, 20, 269-323, and references cited therein.
3. A. M. Tafesh, J. Weiguny, Chem. Rev. 1996, 96, 2035-2052, and references cited therein.
4. E. Drent, P. W. N. M. Van Leeuwen, US Patent 4,474,978, 1984: Eur. Pat. Appl. EP 86,281, 1983; Chem. Abstr. 1984, 100, 6109x.
5. E. Drent, Eur. Pat. Appl. EP 231,045, 1987; Chem. Abstr. 1988, 109, 128605n.
6. J. Stapersma, K. Steernberg, Eur. Pat. Appl. EP 296,686, 1988; Chem. Abstr. 1989, 111, 133802v.
7. A. Bontempi, E. Alessio, G. Chanos, G. Mestroni, J. Mol. Catal. 1987, 42, 67-80.
8. E. Alessio, G. Mestroni, J. Mol. Catal. 1984, 26, 337-340.
9. E. Alessio, G. Mestroni, J. Organomet. Chem. 1985, 291, 117-127.
10. E. Drent, Pure Appl. Chem. 1990, 62, 661-9.
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; Chem. Abstr. 1990, 112, 78160c.
13. 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.
14. 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.
15. P. Wehman, L. Borst, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Mol. Catal. A 1996, 112, 23-36.
16. P. Wehman, L. Borst, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Ber./Recueil 1997, 130, 13-21.
17. P. Wehman, H. M. A. van Donge, A. Hagos, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Organomet. Chem. 1997, 535, 183-193.
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 cited 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, 95-9.
24. R. Santi, A. M. Romano, P. Panella, G. Mestroni, A. Sessanta o Santi, J. Mol. Catal. A 1999, 144, 41-45.
25. P. Leconte, F. Metz, A. Mortreux, J. A. Osborn, F. Paul, F. Petit, A. Pillot, J. Chem. Soc. Chem. Commun. 1990, 1616-1617.
26. a) F. Paul, J. Fischer, P. Ochsenbein, J. A. Osborn, Angew. Chem. Int. Ed. Engl. 1993, 32, 1638-1640;
27. b) F. Paul, J. Fischer, P. Ochsenbein, J. A. Osborn, C. R. Chimie 2002, 5, 267-287.
28. A. Sessanta o Santi, B. Milani, G. Mestroni, E. Zangrando, L. Randaccio, J. Organomet. Chem. 1997, 545-546, 89-91.
29. N. Masciocchi, F. Ragaini, S. Cenini, A. Sironi, Organometallics 1998, 17, 1052-1057.
30. F. Paul, J. Fisher, P. Ochsenbein, J. A. Osborn, Organometallics 1998, 17, 2199-2206.
31. E. Gallo, F. Ragaini, S. Cenini, F. Demartin, J. Organomet. Chem. 1999, 586, 190-195.
32. A. Sessanta o Santi, B. Milani, E. Zangrando, G. Mestroni, Eur. J. Inorg. Chem. 2000, 2351-2354.
33. M. Gasperini, F. Ragaini, S. Cenini, E. Gallo, J. Mol. Catal. A 2003, 204-205, 107-114.
34. F. Ragaini, E. Gallo, S. Cenini, J. Organomet. Chem. 2000, 593-594, 109-118.
35. F. Ragaini, C. Cognolato, M. Gasperini, S. Cenini, Angew. Chem. Int. Ed. 2003, 42, 2886-2889; Angew. Chem. 2003, 115, 2992-2995.
36. F. Ragaini, C. Cognolato, M. Gasperini, S. Cenini, Angew. Chem. Int. Ed. 2003, 42, 2886-2889; Angew. Chem. 2003, 115, 2992-2995.
37. F. Ragaini, M. Gasperini, S. Cenini, Adv. Synth. Catal. 2004, 346, 63-71.
38. J. S. Yadav, G. S. Reddy, M. M. Reddy, H. M. Meshram, Tetrahedron Lett. 1998, 39, 3259-3262.
39. F. Ragaini, Organometallics 1996, 15, 3572-3578.
40. a) H. des Abbayes, H. Alper, J. Am. Chem. Soc. 1977, 99, 98-101;
41. b) H. Alper, D. Des Roches, H. des Abbayes, Angew. Chem. Int. Ed. Engl. 1977, 16, 41-41;
42. c) H. Alper, H.-N. Paik, Nouv. J. Chim. 1978, 2, 245-247;
43. d) H. Alper, L. C. Damude, Organometallics 1982, 1, 579-581;
44. e) H. Alper, M. Gopal, J. Chem. Soc. Chem. Commun. 1980, 821-821.
45. H. Nishida, N. Takada, M. Yoshimura, T. Sonoda, H. Kobayashi, Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604.
46. H. Iwamoto, T. Sonoda, H. Kobayashi, Tetrahedron Lett. 1983, 24, 4703-4706.
47. B. Milani, A. Anzilutti, L. Vicentini, A. Sessanta o Santi, E. Zangrando, S. Geremia, G. Mestroni, Organometallics 1997, 16, 5064-5075.
48. M. Brookhart, B. Grant, A. F. Volpe Jr., Organometallics 1992, 11, 3920-3922.
49. S. R. Bahr, P. Boudjouk, J. Org. Chem. 1992, 57, 5545-5547.
50. [15]
51. F. Ragaini, M. Gasperini, S. Cenini, unpublished results.
52. J. Bergman, P. Sand, Tetrahedron 1990, 46, 6085-6112.
53. M. C. Carreño, J. M. Cuerva, M. Ribarorda, A. M. Echavarren, Angew. Chem. Int. Ed. 1999, 38, 1449-1452.
54. a) F. Ragaini, A. Ghitti, S. Cenini, Organometallics 1999, 18, 4925-4933;
55. b) F. Ragaini, S. Cenini, J. Mol. Catal. A 2000, 161, 31-38.
56. M. Aresta, E. Quaranta, Tetrahedron 1991, 47, 9489-9502.
57. W. V. Konze, B. L. Scott, G. J. Kubas, Chem. Commun. 1999, 1807-1808.
58. a) E. Drent, P. H. M. Budzelaar, Chem. Rev. 1996, 96, 63-81, and references cited therein;
59. b) C. Querci, R. D'Alosio, R. Bortolo, M. Ricci, D. Bianchi, J. Mol. Catal. A 2001, 176, 95-100;
60. c) A. Macchioni, A. Romani, C. Zuccaccia, G. Guglielmetti, C. Querci, Organometallics 2003, 22, 1526-1533.
61. Y. Watanabe, Y. Tsuji, R. Takeuchi, Bull. Chem. Soc. Jpn. 1984, 57, 3011-3012.
62. P. Tavs, Chem. Ber. 1970, 103, 2428-36.
63. C. Yuan, H. Feng, Synthesis 1990, 140-141.
64. M. M. Kabachnik, M. D. Solntseva, V. V. Izmer, Z. S. Novikova, I. P. Beletskaya, Russ. J. Org. Chem. 1998, 34, 93-97; Zh. Org. Khim. 1998, 34, 106-111.
65. M. M. Kabachnik, M. D. Solntseva, V. V. Izmer, Z. S. Novikova, I. P. Beletskaya, Russ. J. Org. Chem. 1998, 34, 93-97; Zh. Org. Khim. 1998, 34, 106-111.