Efficient and convenient method for the synthesis of N-arylhydrazones using a palladium-catalyzed bond-forming reaction

Synthetic Communications

Volumn 36, Issue 8, 2006, Pages 1123-1129

  Mauger, Christelle ^a   Mignani, Gérard ^a  

^a Rhodia Recherches   (France)

Author keywords

Aryl chlorides; Buchwald ligands; Cross coupling; Hydrazone; Palladium; Phosphines

Indexed keywords

BENZOPHENONE DERIVATIVE; CARBON; HYDRAZONE DERIVATIVE; N (2 CHLOROPHENYL)BENZOPHENONE HYDRAZONE; N (2 TOLYL)BENZOPHENONE HYDRAZONE; N (4 CHLOROPHENYL)BENZOPHENONE HYDRAZONE; N (4 FLUOROPHENYL)BENZOPHENONE HYDRAZONE; N (4 METHOXYPHENYL)BENZOPHENONE HYDRAZONE; N (4 TOLYL)BENZOPHENONE HYDRAZONE; N (4 TRIFLUOROMETHYLPHENYL)BENZOPHENONE HYDRAZONE; N PHENYLBENZOPHENONE HYDRAZONE; NITROGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; CROSS COUPLING REACTION; REPRODUCIBILITY; SPECTROSCOPY; SYNTHESIS;

EID: 33644997910     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500501292     Document Type: Article

References (25)

1. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
2. (a) Baranano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287;
3. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
4. (a) Gilchrist, T. L. J. Chem. Soc., Perkin Trans 1 1999, 2849;
5. (b) Müller, E. Methoden der Organischen Chemie 1967, Houben-Weyl band X12;
6. (c) Robinson, B. Chem. Rev. 1963, 63, 373;
7. (d) Ishii, H. Acc Chem Res. 1981, 14, 233;
8. (e) Hughes, D. L. Org. Prep Proceed. Int. 1993, 25, 607.
9. (a) Robinson, B. The Fischer Indole Synthesis; Wiley: Chichester, 1982;
10. (b) Robinson, B. Chem. Rev. 1969, 69, 227.
11. (a) Negwer, M. Organic-Chemical Drugs and Their Synonyms: An international survey, 7th ed.; Akademie Verlag GmbH: Berlin, 1994;
12. (b) Montgomery, J. H. Agrochemicals Desk Reference: Environmental Data; Lewis Publishers: Chelsea, MI, 1993;
13. (c) Loutfy, R. O.; Hsiao, C. K.; Kazmaier, P. M. Photograph. Sci. Eng. 1983, 27, 5;
14. (d) D'Aprano, G.; Leclerc, M.; Zotti, G.; Schiavon, G. Chem. Mater. 1995, 7, 33;
15. (e) Czarnik, A. W. Acc. Chem. Res. 1996, 29, 112.
16. Haddad, N.; Salvagno, A.; Busacca, T. Tetrahedron Lett. 2004, 45, 5935.
17. (a) Mauger, C. C.; Mignani, G. A. Adv. Synth. Catal. 2005, 347 (6), 773;
18. (b) Mauger, C. C.; Mignani, G. A. Org. Proc. Res. Dev. 2004, 8 (6), 1065.
19. Tomori, H.; Fox, J. M.; Buchwald, S. L. Buchwald has proven the high efficiency of MePhos toward the carbon-nitrogen coupling reaction. J. Org. Chem. 2000, 65, 5334.
20. Littke, A. F.; Fu, G. C. For are centre view dealing with palladium-catalyzed coupling reactions of arylchlorides. Angew. Chem., Int. Ed. 2002, 41, 4176.
21. (a) Buchwald, S. L. Adv. Synth. Catal. 2001, 343, 789;
22. (b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
23. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 1212 (44), 10251.
24. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
25. Kohling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5 (18), 3213.