Comparing the reactivity of the 4- and 5-positions of 2-phenylthiazoles in stille cross-coupling reactions

Synlett

Volumn , Issue 19, 2007, Pages 2975-2978

  Hämmerle, Johanna ^a   Schnürch, Michael ^a   Stanetty, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Cross coupling; Heterocycles; Palladium; Stille reaction; Thiazoles

Indexed keywords

2 PHENYLTHIAZOLE DERIVATIVE; BROMINE; HALIDE; IODINE; PALLADIUM; THIAZOLE DERIVATIVE; TIN; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CROSS COUPLING REACTION; SYNTHESIS;

EID: 37249067479     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990972     Document Type: Article

References (39)

1. (a) Rivkin, A.; Cho, Y. S.; Gabarda, A. E.; Yoshimura, F.; Danishefsky, S. J. J. Nat. Prod. 2004, 67, 139.
2. (b) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem. Int. Ed. 1998, 37, 2014.
3. (c) Bach, T.; Heuser, S. Angew. Chem. Int. Ed. 2001, 40, 3184.
4. (d) Plazzi, P. V.; Bordi, F.; Silva, C.; Morini, G.; Caretta, A.; Barocelli, E.; Vitali, T. Eur. J. Med. Chem. 1995, 30, 881.
5. (e) Ganesh, T.; Schilling, J. K.; Palakodety, R. K.; Ravindra, R.; Shanker, N.; Bane, S.; Kingston, D. G. I. Tetrahedron 2003, 59, 9979.
6. (f) Shao, J.; Panek, J. S. Org. Lett. 2004, 6, 3083.
7. (a) Hattinger, G.; Stanetty, P.; Eberle, M. UK Patent Appl., GB 2369359, 2002; Chem. Abstr. 2002, 137, 216957.
8. (b) Stanetty, P.; Roehrling, J.; Schnürch, M.; Mihovilovic, M. D. Tetrahedron 2006, 62, 2380.
9. (c) Stanetty, P.; Hattinger, G.; Schnürch, M.; Mihovilovic, M. D. J. Org. Chem. 2005, 70, 5215.
10. (d) Mueller, U.; Eberle, M.; Pillonel, C.; Lutz, W.; Stanetty, P. PCT Int. Appl., WO 2003029249, 2003; Chem. Abstr. 2003, 138, 304297.
11. (a) Hantzsch, A. Ber. Dtsch. Chem. Ges. 1888, 21, 942.
12. (b) In Science of Synthesis, Vol. 11; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart Germany, 2002, 627.
13. Carter, J. S.; Rogier, D. J.; Graneto, M. J.; Seibert, K.; Koboldt, C. M.; Zhang, Y.; Talley, J. J. Bioorg. Med. Chem. Lett. 1999, 9, 1167.
14. (a) Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; Negishi, E.; de Meijere, A., Eds.; Wiley: Hoboken N.J., 2002.
15. (b) Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2; Negishi, E.; de Meijere, A., Eds.; Wiley: Hoboken N.J., 2002.
16. (c) De Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Vol. 1; Wiley-VCH: Weinheim Germany, 2004.
17. (d) De Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Vol. 2; Wiley-VCH: Weinheim Germany, 2004.
18. (e) Schnürch, M.; Flasik, R.; Khan, A.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 15, 3283.
19. (a) Bach, T.; Heuser, S. Tetrahedron Lett. 2000, 41, 1707.
20. (b) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 1363.
21. (a) Stille, J. K. Angew. Chem. 1986, 98, 504.
22. (b) Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 4704.
23. Stanetty, P.; Schnürch, M.; Mihovilovic, M. D. J. Org. Chem. 2006, 71, 3754.
24. Erlenmeyer, H.; Becker, C.; Sorkin, E.; Bloch, H.; Suter, E. Helv. Chim. Acta 1947, 30, 2058.
25. Begtrup, M.; Hansen, L. B. L. Acta Chem. Scand. 1992, 46, 372.
26. For reviews of halogen dance (HD) reactions, see: (a) Schnürch, M.; Spina, M.; Khan, A. F.; Mihovilovic, M. D.; Stanetty, P. Chem. Soc. Rev. 2007, 36, 1046.
27. (b) Nora de Souza, M. V. Curr. Org. Chem. 2007, 11, 637.
28. (c) Duan, X.-F.; Zhang, Z.-B. Heterocycles 2005, 65, 2005.
29. (d) Fröhlich, J. Prog. Heterocycl. Chem. 1994, 6, 1.
30. (e) Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139 .
31. For HD reactions on thiazole, see: (f) Stanetty, P.; Schnürch, M.; Mereiter, K.; Mihovilovic, M. D. J. Org. Chem. 2005, 70, 567.
32. (g) Stangeland, E. L.; Sammakia, T. J. Org. Chem. 2004, 69, 2381.
33. (h) Holzweber, M.; Schnürch, M.; Stanetty, P. Synlett 2007, in press.
34. Crawforth, C. M.; Fairlamb, I. J. S.; Kapdi, A. R.; Serrano, J. L.; Taylor, R. J. K.; Sanchez, G. Adv. Synth. Catal. 2006, 348, 405.
35. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411.
36. 16
37. (a) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
38. (b) Grushin, V. V. Organometallics 2000, 19, 1888.
39. Vernin, G.; Aune, J. P.; Dou, H. J. M.; Metzger, J. Bull. Soc. Chim. Fr. 1967, 4523.