Selenium-catalyzed reductive carbonylation of 2-nitrophenols to 2-benzoxazolones

European Journal of Organic Chemistry

Volumn , Issue 8, 2005, Pages 1675-1679

  Wang, Xiaofang ^a   Ling, Gang ^a   Xue, Yan ^a   Lu, Shiwei ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Carbonylation; Nitrophenols; Phase transfer catalysis; Reduction; Selenium

Indexed keywords

EID: 18144405383     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400561     Document Type: Article

References (36)

1. M. Seki, K. Mori, Eur. J. Org. Chem. 1999, 2965-2967.
2. EP 1251128 AI, 23 Oct 2002.
3. L. Quaranta, O. Corminboeuf, P. Renaud, Org. Lett. 2002, 4, 39-42.
4. Y. K. Wu, X. Shen, C. J. Tang, Z. L. Chen, Q. Hu, W. Shi, J. Org. Chem. 2002, 67, 3802-3810.
5. G. V. Boyd, A. R. Katritzky, C. W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1984, vol. 8, p. 178.
6. F. Yue, B. Toshihide, O. Yoshio, J. Catal. 2001, 197, 91-97.
7. U. Romano, R. Tesel, M. M. Mauri, P. Rebora, Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 396-403.
8. B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
9. B. Gabriele, R. Mancuso, G. Salerno, M. Costa, J. Ore. Chem. 2003, 68, 601-604.
10. J. E. McCusker, C. A. Grasso, A. D. Main, L. McElwee-White, Org. Lett. 1999, 1, 961-964.
11. F. Qian, J. McCusker, Y. Zhang, A. D. Main, M. Chlebowski, M. Kokka, L. McElwee-White, J. Org. Chem. 2002, 67, 4086-4092.
12. N. Sonoda, T. Yasuhara, K. Kondo, T. Ikeda, S. Tsutsumi, J. Am. Chem. Soc. 1971, 93, 6344.
13. K. Kondo, S. Yokoyama, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem. Int. Ed. Engl. 1979, 18, 691-692.
14. T. Yoshida, N. Kambe, S. Murai, N. Sonoda, Bull. Chem. Soc. Jpn. 1987, 60, 1793-1799.
15. T. Yoshida, N. Kambe, S. Murai, N. Sonoda, Tetrahedron Lett. 1986, 27, 3037-3040.
16. P. Braunstein, J. Kervennal, J. L. Richert, Angew. Chem. Int. Ed. Engl. 1985, 24, 768-770.
17. P. Braunstein, R. Devenish, P. Gallezot, B. T. Heaton, C. J. Humphreys, Angew. Chem. Int. Ed. Engl. 1988, 27, 927-929.
18. S. Cenini, S. Console, C. Crotti, S. Tollari, J. Orgnomet. Chem. 1993, 451, 157-162.
19. T. Miyata, N. Kambe, S. Murai, N. Sonoda, Nippon kakaku Kaishi 1987, 7, 1332-1337.
20. JP 83225072, JP 82102876.
21. Y. Yang, S. W. Lu, Tetrahedron Lett. 1999, 40, 4845-4846.
22. H. S. Kim, Y. J. Kim, H. Lee, S. D. Lee, C. S. Chin, J. Mol. Catal. 1999, 184, 526-534.
23. J.Z. Chen, G. Ling, S.W. Lu, Eur. J. Org. Chem. 2003, 17, 3446-3452.
24. G. Ling, J. Z. Chen, S. W. Lu, Cuihua Xuebao 2003, 24, 5-6.
25. N. Yutaka, N. Yoshitaka, S. Noboru, Synlett 2004, 5, 886-888.
26. J. T. Mei, Y. Yang, Y. Xue, S. W. Lu, J. Mol. Catal. A: Chem. 2003, 191, 135-139.
27. We performed the reductive carbonylation of nitrobenzene with nBuOH under atmospheric pressure. Diphenylurea was obtained instead of carbamate.
28. L. Mcssaoud, Y. Said, D. Patrick, P. Jacques, H. L. Daniel, Heterocycles 1999, 51, 1929-1943.
29. W. J. Close, B. D. Tiffany, M. A. Spielman, J. Am. Chem. Soc. 1949, 71, 1265-1268.
30. W. J. Schnabel, E. Kober, J. Org. Chem. 1969, 34, 1162-1165.
31. O. Prakash, H. Batra, H. Kaur, P. K. Sharma, V. Sharma, S. P. Singh, R. M. Moriarty, Synthesis 2001, 4, 541-543.
32. T. Kihlberg, F. Karimi, B. Långstrøm, J. Org. Chem. 2002, 67, 3687-3682.
33. X. F. Wang, S. W. Lu, Z. K. Yu, Adv. Synth. Catal. 2004, 346, 929-932.
34. C.V. Rode, S. P. Gupta, R. V. Chaudhari, C. D. Pirozhkov. A. L. Lapidus, J. Mol. Catal. 1994, 91, 195-206.
35. A. F. M. Iqbal, J. Org. Chem. 1972, 37, 2791-2793.
36. S. M. Islam, D. Mal, B. K. Palit, C. R. Saha, J. Mol. Catal. A: Chem. 1999, 142, 169-181.