Efficient Heck arylations of cyclic and acyclic acrylate derivatives using arenediazonium tetrafluoroborates. A new synthesis of the antidepressant drug (±)-paroxetine

Organic Letters

Volumn 8, Issue 8, 2006, Pages 1657-1660

  Pastre, Julio Cezar ^a   Correia, Carlos Roque Duarte ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDEPRESSANT AGENT; BORIC ACID; DIAZONIUM COMPOUND; PAROXETINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTIDEPRESSIVE AGENTS; BORATES; CATALYSIS; DIAZONIUM COMPOUNDS; MOLECULAR STRUCTURE; PAROXETINE; STEREOISOMERISM;

EID: 33646459933     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060248e     Document Type: Article

References (34)

1. (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
2. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: Hoboken, New York, 2002.
3. (c) Cross-Coupling Reactions. A Practical Guide; Miyaura, N., Ed.; Springer: Berlin, 2002.
4. (a) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
5. (b) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
6. (c) de Vries, J. G. Can. J. Chem. 2001, 79, 1086.
7. (d) Whitcombe, N. J.; Hii, K. K. M.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
8. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
9. (a) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.
10. (b) Kikukawa, K.; Matsuda, T. Chem. Lett. 1977, 159.
11. (a) Garcia, A. L. L.; Carpes, M. J. S.; Montes de Oca, A. C. B.; Santos, M. A. G.; Santana, C. C.; Correia, C. R. D. J. Org. Chem. 2005, 70, 1050.
12. (b) Garcia, A. L. L.; Correia, C. R. D. Tetrahedron Lett. 2003, 44, 1553.
13. (c) Severino, E. A.; Costenaro, E. R.; Garcia, A. L. L.; Correia, C. R. D. Org. Lett. 2003, 5, 305.
14. (a) Gurtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107.
15. (b) Calò, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. J. Org. Chem. 2003, 68, 2929.
16. Calò, V.; Nacci, A.; Monopoli, A.; Detomaso, A.; Iliade, P. Organometallics 2003, 22, 4193.
17. (c) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
18. Part of this work was presented at the XXVIII Annual Meeting of the Brazilian Chemical Society, May 2005, and at the XI Brazilian Meeting on Organic Synthesis, Canela, Brazil, August/September 2005.
19. Renin inhibitors: (a) Oefner, C.; Binggeli, A.; Breu, V.; Bur, D.; Clozel, J.-P.; D'Arcy, A.; Dorn, A.; Fischli, W.; Gruninger, F.; Guller, R.; Hirth, G.; Marki, H. P.; Mathews, S.; Muller, M.; Ridley, R. G.; Stadler, H.; Vieira, E.; Wilhelm, M.; Winkler, F. K.; Wostl, W. Chem. Biol. 1999, 6, 127.
20. (b) Bursavich, M. G.; West, C. W.; Rich, D. H. Org. Lett. 2001, 3, 2317.
21. (a) Wagstaff, A. J.; Cheer, S. M.; Matheson, A. J.; Ormrod, D.; Goa, K. L. CNS Drugs 2002, 16, 425-434.
22. (b) Bourin, M.; Chue, P.; Guillon, Y. CNS Drug Rev. 2001, 7, 25.
23. Almansa, C.; Gómez, L. A.; Cavalcanti, F. L.; de Arriba, A. F.; Rodríguez, R.; Carceller, E.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 1996, 39, 2197.
24. Winkler, J. D.; Axten, J.; Hammach, A. H.; Kwak, Y.-S.; Lengweiler, U.; Lucero, M. J.; Houk, K. N. Tetrahedron 1998, 54, 7045.
25. Carpes, M. J. S.; Correia, C. R. D. Synlett 2000, 7, 1037.
26. (a) Yamada, S.; Jahan, I. Tetrahedron Lett. 2005, 46, 8673.
27. (b) Takasu, K.; Nishida, N.; Tomimura, A.; Ihara, M. J. Org. Chem. 2005, 70, 3957.
28. (c) Cheng, C.-Y.; Chang, B.-R.; Tsai, M.-R.; Chang, M.-Y.; Chang, N.-C. Tetrahedron 2003, 59, 9383.
29. (d) Greenhalgh, D. A.; Simpkins, N. S. Synlett 2002, 12, 2074.
30. Hoesl, C. E.; Hofner, G.; Wanner, K. T. Tetrahedron 2004, 60, 307.
31. Shih, K.-S.; Liu, C.-W.; Hsieh, Y.-J.; Chen, S.-F.; Ku, H.; Liu, L. T.; Lin, Y.-C.; Huang, H.-L.; Wang, C.-L. J. Heterocycles 1999, 51, 2439.
32. Faruk, F. A.; Martin, R. T. U.S. Patent 4902801, 1990; Chem. Abstr. 1988, 109, 6427.
33. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004.
34. During the preparation of this manuscript, a report dealing with the Heck arylation of substituted acrylates (Baylis-Hillman adducts) using arenediazonium salts appeared in the literature (Antunes, O. A. C. et al. Tetrahedron Lett. 2006, 47, 1325).