Selective and environmentally friendly methodologies based on the use of electrochemistry for fine chemical preparation: An efficient synthesis of N,N′-disubstituted ureas

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 7137-7139

  Chiarotto, Isabella ^a   Feroci, Marta ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDATIVE CARBONYLATION;

AROMATIC COMPOUNDS; ATMOSPHERIC PRESSURE; CARBON MONOXIDE; CARBONYLATION; CATALYSTS; GRAPHITE ELECTRODES; OXIDATION; PALLADIUM; SYNTHESIS (CHEMICAL);

ELECTROCHEMISTRY;

ALIPHATIC AMINE; AROMATIC AMINE; CARBON MONOXIDE; PALLADIUM; UREA DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; ELECTROCHEMISTRY; SYNTHESIS;

EID: 0041336692     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034750d     Document Type: Article

References (30)

1. Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N,; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N,; Chang, C. H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Viitanen, S. Science 1994, 263, 380-384.
2. Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; DeLucca, G. V.; Eyermann, C. J.; Chang, C. H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L. Z.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Li, R. H.; Markwalder, J. A.; Seitz, S. P.; Sharpe, T. R.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L. Y.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; Erickson-Viitanen, S.; Hodge, C. N. J. Med. Chem. 1996, 39, 3514-3525.
3. Dragovich, P. S.; Barker, J. E.; French, J.; Imbacuan, M.; Kalish, V. J. ; Kissinger, C. R.; Knighton, D. R.; Lewis, C. T.; Moomaw, E. W.; Parge, H. E.; Pelletier, L. A. K.; Prins, T. J.; Showalter, R. E.; Tatlock, J. H.; Tucker, K. D.; Villafranca, J. E. J. Med. Chem. 1996, 39, 1872-1884.
4. For use of phosgene and its derivatives, see: Hegarty, A. F.; Drennan, L. J. In Comprehensive Organic Funcional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 6, pp 499-526. Guichard, G.; Semetery, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705. Majer, P.; Randal, R. S. J. Org. Chem. 1994, 59, 1937-1938. Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807.
5. For use of phosgene and its derivatives, see: Hegarty, A. F.; Drennan, L. J. In Comprehensive Organic Funcional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 6, pp 499-526. Guichard, G.; Semetery, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705. Majer, P.; Randal, R. S. J. Org. Chem. 1994, 59, 1937-1938. Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807.
6. For use of phosgene and its derivatives, see: Hegarty, A. F.; Drennan, L. J. In Comprehensive Organic Funcional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 6, pp 499-526. Guichard, G.; Semetery, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705. Majer, P.; Randal, R. S. J. Org. Chem. 1994, 59, 1937-1938. Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807.
7. For use of phosgene and its derivatives, see: Hegarty, A. F.; Drennan, L. J. In Comprehensive Organic Funcional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 6, pp 499-526. Guichard, G.; Semetery, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705. Majer, P.; Randal, R. S. J. Org. Chem. 1994, 59, 1937-1938. Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807.
8. Satchell, R. S.; Satchell, D. P. N. Chem. Soc. Rev. 1975, 4, 231-250.
9. Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420-6423.
10. Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569-4572.
11. McCusker, J. E.; Grasso, C. A.; Main, A. D.; McElwee-White, L. Org. Lett. 1999, 1, 961-964. McCusker, J. E.; Qian, F.; McElwee-White, L. J. Mol. Catal. A.: Chem. 2000, 159, 11-17. McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. J. Org. Chem. 2000, 65, 5216-5222.
12. McCusker, J. E.; Grasso, C. A.; Main, A. D.; McElwee-White, L. Org. Lett. 1999, 1, 961-964. McCusker, J. E.; Qian, F.; McElwee-White, L. J. Mol. Catal. A.: Chem. 2000, 159, 11-17. McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. J. Org. Chem. 2000, 65, 5216-5222.
13. McCusker, J. E.; Grasso, C. A.; Main, A. D.; McElwee-White, L. Org. Lett. 1999, 1, 961-964. McCusker, J. E.; Qian, F.; McElwee-White, L. J. Mol. Catal. A.: Chem. 2000, 159, 11-17. McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. J. Org. Chem. 2000, 65, 5216-5222.
14. Giannoccaro, P.; Nobile, C. F.; Mastrorilli, C.; Ravasio, J. J. Organomet. Chem. 1991, 419, 251-258,
15. Srivastva, S. C.; Shrimal, A. K.; Srivastva, A. J. Organomet. Chem. 1991, 414, 65-69.
16. Bassoli, A.; Rindone, B.; Tollari, S.; Chioccara, F. J. Mol. Catal. 1990, 60, 41-48.
17. Mulla, S. A. R.; Gupte, S. P.; Chaudhari, R. V. J. Mol. Catal. 1991, 67, L7-L10.
18. Mulla, S. A. R.; Rode, C. V.; Kelkar, A. A.; Gupte, S. P. J. Mol. Catal. A.: Chem. 1997, 122, 103-109.
19. Valli, V. L. K.; Alper, H. Organometallics 1995, 14, 80-82. Gupte, S. P. ; Chaudhari, R. V. J. Catal. 1988, 114, 246-258.
20. Valli, V. L. K.; Alper, H. Organometallics 1995, 14, 80-82. Gupte, S. P. ; Chaudhari, R. V. J. Catal. 1988, 114, 246-258.
21. Pri-Bar, I.; Alper, H. Can. J. Chem. 1990, 68, 1544-1547. Shi, F.; Deng, Y.; SiMa, T.; Yang, H. Tetrahedron Lett. 2001, 42, 2161-2163.
22. Pri-Bar, I.; Alper, H. Can. J. Chem. 1990, 68, 1544-1547. Shi, F.; Deng, Y.; SiMa, T.; Yang, H. Tetrahedron Lett. 2001, 42, 2161-2163.
23. Giannoccaro, P. J. Organomet. Chem. 1987, 336, 271-278.
24. Yang, H.; Deng, Y.; Shi, F. J. Mol. Catal. A.: Chem. 2001, 176, 73-78.
25. Chiarotto, I.; Carelli, I. Synth. Commun. 2002, 32, 881-886.
26. Chiarotto, I.; Feroci, M. Tetrahedron Lett. 2001, 42, 3451-3453.
27. The working potential was slightly more positive than the oxidation peak potential of Pd(0): Carelli, I.; Chiarotto, I.; Cacchi, S.; Pace, P.; Amatore, C.; Jutand, A.; Meyer, G. Eur. J. Org. Chem. 1999, 1471-1473.
28. Amatore, C.; Jutand, A.; Meyer, G.; Carelli, I.; Chiarotto, I. Eur. J. Inorg. Chem. 2000, 8, 1855-1859.
29. Amines were purchased from commercial sources and were purified prior to use. Standard of disubstituted ureas and oxamides synthesized in this paper, are commercially available. The ureas and oxamides were characterized by comparison of infrared, nuclear magnetic resonance, and mass spectra with those for authentic materials and literature data.
30. The HPLC analysis of the electrolysis carried out in DMF solvent showed the presence of both isocyanate and carbammic acid, but no qualitative analysis was possible because carbammic acid can be also produced, by hydrolysis of isocyanate, in the HPLC column.