Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles

Journal of Organic Chemistry

Volumn 73, Issue 8, 2008, Pages 3278-3280

  Besselièvre, François ^a,b   Mahuteau Betzer, Florence ^a   Grierson, David S ^c   Piguel, Sandrine ^a,b  

^a INSTITUT CURIE   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; LEUSEN OXAZOLE RING SYNTHESIS;

CATALYST ACTIVITY; CHEMICAL REACTIONS; LIGANDS;

PALLADIUM COMPOUNDS;

ALKALOID; BALSOXIN; COPPER; FUNCTIONAL GROUP; O METHYL HALFORDINOL; OXAZOLE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TEXALINE; TEXAMINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CROSS COUPLING REACTION; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOSPECIFICITY; SYNTHESIS;

BROMIDES; CATALYSIS; COPPER; LIGANDS; MICROWAVES; MOLECULAR STRUCTURE; OXAZOLES; PALLADIUM;

EID: 42149089013     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7027135     Document Type: Article

References (29)

1. Palmer, D. C.; Venkatraman, S. In Oxazoles: Synthesis, Reactions and Spectroscopy, Part A; J. Wiley & Sons: Hoboken, NJ, 2004.
2. Zificsak, C. A.; Hlasta, D. J. Tetrahedron 2004, 60, 8991.
3. For recent reviews of heteroarenes and arenes direct arylation, see: (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
4. (b) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
5. (c) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
6. (d) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35.
7. (a) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 1970.
8. (b) Bellina, F.; Cauteruccio, S.; Rossi, R. J. Org. Chem. 2007, 72, 8543.
9. Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
10. Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449.
11. For very recent examples, see: (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404 and references cited therein.
12. (b) Turner, G. L.; Morris, J. A.; Greaney, M. F. Angew. Chem., Int. Ed. 2007, 46, 7996 and references cited therein.
13. (c) For a mechanistic discussion, see: Sanchez, R. S.; Zhuravlev, A. J. Am. Chem. Soc. 2007, 129, 5824.
14. Hoarau, C.; Du Fou de Kerdaniel, A.; Bracq, N.; Grandclaudon, P.; Couture, A.; Marsais, F. Tetrahedron Lett. 2005, 46, 8573.
15. Li, X.; Murray, W. V.; Macielag, M. J.; Guan, Q. U.S. Patent 113522 A1, 2005.
16. Van Leusen, A. M.; Hoogenboom, B. E.: Siderius, H. Tetrahedron Lett. 1972, 23, 2369.
17. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
18. 3 (2 equiv) as the base without ligand in DMF at 150°C.
19. Kappe, O. C.; Stadler, A.; Mannhold, R. In Microwaves in organic and medicinal chemistry; Wiley-VCH: Weinheim, Germany, 2006.
20. During the preparation of this manuscript, a microwave-assisted Pd-catalyzed direct arylation of triazoles was published: Iwasaki, M.; Yorimitsu, H.; Oshima, K. Chem. Asian J. 2007, 2, 1430.
21. No product instability was observed under the reaction conditions. In fact, exposing product 2a to the reaction conditions for 30 min led to full recovery.
22. Compounds 2k, 2l, and 2m were obtained in, respectively, 57%, 55%, and 52% yields after 15 min heating.
23. Dominguez, X. A.; de la Fuente, G.; Gonzalez, A. G.; Reina, M.; Timon, I. Heterocycles 1988, 27, 35.
24. Ciddens, A. C.; Boshoff, H. I. M.; Franzblau, S. G.; Barry, C. E.; Copp, B. R. Tetrahedron Lett. 2005, 46, 7355.
25. Burke, B.; Parkins, H.; Talbot, A. M. Heterocycles 1979, 12, 349.
26. Hodgetts, K. J; Kershaw, M. T. Org. Lett. 2002, 4, 2905.
27. Kozikowski, A. P.; Ames, A. J. Org. Chem. 1980, 45, 2548.
28. Kulkarni, B. A.; Ganesan, A. Tetrahedron Lett. 1999, 40, 5633.
29. Nicolaou, K. C.; Hao, J.; Reddy, M. V.; Rao, P. B.; Rassias, G.; Snyder, S. A.; Huang, X.; Chen, D. Y.-K.; Brenzovich, W. E.; Giuseppone, N.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2004, 126, 12897.