Aromatization of enamines promoted by a catalytic amount of Pd/C. Synthesis of aromatic amines

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2557-2559

  Cossy, Janine ^a   Belotti, Damien ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041382866     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026184z     Document Type: Article

References (27)

1. (a) D'Aproano, G.; Schiavon, G.; Zotti, G.; Leclerc, M. Chem. Mater. 1995, 7, 33.
2. Loutfy, R. O.; Hsiao, C. K.; Kazmaier, P. M. Photogr. Sci. Eng. 1983, 27, 5.
3. Negwer, M. Organic Chemical Drugs and their Synonyms, 7th ed.; Akademie Verlag GmbH: Berlin, 1994.
4. Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanisms: VCH: New York, 1989.
5. (b) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203.
6. (a) Kovacic, P.; Russell, R. L.; Bennett, R. P. J. Am. Chem. Soc. 1964, 86, 1588 and references therein.
7. (b) Olah, G. A.; Ernst, T. D. J. Org. Chem. 1989, 54, 1203.
8. (a) Ibata, T.; Isogami, Y.; Toyoda, J. Chem. Lett. 1987, 1187.
9. (b) Chiacchiera, S. M.; Singh, J. O.; Anunziata, J. D.; Silber, J. J. J. Chem. Soc., Perkin Trans. 2 1987, 987.
10. (c) Pardisi, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 2.1.
11. Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 2.3.
12. (a) Norris, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 2.2.
13. (b) Kim, J. K.; Bunnett, J. F. J. Am. Chem. Soc. 1970, 92, 7463.
14. Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001.
15. Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. J. Am. Chem. Soc. 1974, 96, 7812.
16. Marcini, P.; Liso, G.; Reho, A. J. Org. Chem. 1975, 40, 3453.
17. Lane, C. F. Synthesis 1975, 135.
18. (a) Hartwig, J. Angew. Chem. 1998, 37, 2046 and references therein.
19. (b) Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618.
20. (c) Alcazar-Roman, L. M.; Harwig, J. F. J. Am. Chem. Soc. 2001, 123, 12905.
21. (d) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
22. (e) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
23. Moskalev, N.; Makosza, M. J. Chem. Soc., Chem. Commun. 2001, 1248.
24. Srinivas, G.; Periasamy, M. Tetrahedron Lett. 2002, 43, 2785.
25. Ishikaura, T.; Uedo, E.; Tani, R.; Saito, S. J. Org. Chem. 2001, 66, 186.
26. 0). The resulting black mixture was stirred and refluxed for 4-12 h (GC/ MS monitoring). After cooling to room temperature, the suspension was filtered through Celite, which was washed with AcOEt. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel to give the aromatic amine.
27. Hünig, S.; Lücke, E.; Brenninger, W. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, pp 808-809.