Halogen dance and sequential cross-coupling on 2-anilinothiazoles

Letters in Organic Chemistry

Volumn 6, Issue 2, 2009, Pages 171-174

  Khan, Ather Farooq ^a   Schnürch, Michael ^a   Mihovilovic, Marko D ^a   Stanetty, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Cross couplings; Halogen dance; Pd catalysis; Sequential cross couplings; Thiazole

Indexed keywords

EID: 67650896884     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809787582780     Document Type: Article

References (47)

1. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture; Pozharsky, A. F.; Soldatenkov, A. T.; Katritzky, A. R. Eds.; John Wiley and Sons, Chichester, England, 1997.
2. (a) Takayama, H.; Kato, K.; Kimura, M.; Akita, H. Heterocycles, 2007, 71, 75.
3. (b) Altmann, K.-H.; Pfeiffer, B.; Arseniyadis, S.; Pratt, B. A.; Nicolaou, K. C. ChemMedChem, 2007, 2, 396.
4. (c) Mueller, H. M.; Delgado, O.; Bach, T. Angew. Chem. Int. Ed., 2007, 46, 4771.
5. (d) Delgado, O.; Heckmann, G.; Mueller, H. M.; Bach, T. J. Org. Chem., 2006, 71, 4599.
6. (e) Jin, Z. Nat. Prod. Rep., 2006, 23, 464.
7. (f) de Souza, M J. Sulfur Chem., 2005, 26, 429.
8. (g) Hughes, R. A.; Thompson, S. P.; Alcarez, L.; Moody, C. J. J. Am. Chem. Soc., 2005, 127, 15644.
9. (h) Jin, Z. Nat. Prod. Rep., 2005, 22, 196.
10. (a) Dunkel, R.; Elbe, H.-L.; Greul, J. N.; Hartmann, B.; Gayer, H.; Seitz, T.; Wachendorff,-Neumann, U.; Dahmen, P.; Kuck, K.-H. PTC Int. Appl. WO2006061215, 2006; Chem. Abstr., 145, 62881.
11. (b) Murakami, H.; Takii, S.; Mizuno, M. Jpn. Kokai Tokkyo Koho JP 200466855, 2005; Chem. Abstr., 143, 306303.
12. (c) Mueller, U.; Eberle, M.; Pillonel, C.; Lutz, W.; Stanetty, P. PCT Int. Appl. WO2003029249, 2003; Chem. Abstr. 138, 304297.
13. (d) Doemling, A.; Kolb, J. Ger. Offen. DE10134478, 2003; Chem. Abstr., 138, 137301
14. (a) Schaumann, E., Ed.; Science of Synthesis, Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom; Georg Thieme Verlag, Stuttgart, Germany, 2002, Vol. 11, p. 627.
15. Hantzsch, A. Ber. Dtsch. Chem. Ges., 1888, 21, 942.
16. (b) Prakash, R.; Kumar, A.; Aggarwal, R.; Prakash, O.; Singh, S. P. Synth. Commun., 2007, 37, 2501.
17. (c)Egan, R. S.; Tadanier, J.; Garmaise, D. L.; Gaunce, A. P. J. Org. Chem., 1968, 33, 4422.
18. (d) Babadjamian, A.; Metzger, J.; Chanon, M. J. Heterocycl. Chem., 1975, 12, 643.
19. (a) Negishi, E.; de Meijere, A., Eds.; Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Inc., Hoboken, N. J. 2002, Vol. 1&2.
20. b) Meijere, A.; Diederich, F. Eds.; Metal-Catalyzed Cross-Coupling Reactions 2nd ed, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany 2004; Vol. 1&2.
21. [7] (a) Prasad, A. S. B.; Stevenson, T. M.; Citineni, J. R.; Nyzam, V.; Knochel, P. Tetrahedron, 1997, 53, 7237.
22. (b) Bach, T.; Heuser, S. Angew. Chem. Int. Ed., 2001, 40, 3184.
23. (c) Stanetty, P; Schnürch, M; Mihovilovic, M. D. J. Org. Chem. 2006, 71, 3754.
24. (d) Hodgetts, K. J; Kershaw, M. T. Org. Lett., 2002, 4, 1363.
25. (e) Nicolaou, K. C; Ritzen, A; Namoto, K; Buey, R. M; Diaz, J. F.; Andreu, J. M.; Wartmann, M; Altmann, K. H; OBrate, A; Giannakakou, P. Tetrahedron, 2002, 58, 6413.
26. (f) Ganesh, T; Schilling, J. K; Palakodety, R. K; Ravindra, R; Shanker, N; Bane, S; Kingston, D. G. I. Tetrahedron, 2003, 59, 9979.
27. (g) Moreno I.; Tellitu, I; Dominguez, E; SanMartin, R. Eur. J. Org. Chem., 2002, 2126.
28. (h) Schnürch, M.; Spina, M.; Khan, A. F.; Flasik, R.; Mihovilovic M. D.; Stanetty, P. Eur. J. Org. Chem., 2006, 3283.
29. For reviews on the HD reaction see: (a) Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139.
30. b) Fröhlich, J. Prog. Het. Chem. 1994, 6, 1.
31. c) Duan, X; Zhang, Z. Heterocycles, 2005, 65, 2005.
32. d) Schnürch, M.; Spina, M; Khan, A. F; Mihovilovic, M. D; Stanetty, P. Chem. Soc Rev., 2007, 36, 1046.
33. For HD reactions on thiazole see a) Stangeland, E. L.; Sammakia, T. J. Org. Chem., 2004, 69, 2381.
34. b) Holzweber, M.; Schnürch, M.; Stanetty, P. Synlett, 2007, 19, 3016.
35. c) Stanetty, P.; Schnürch, M.; Mereiter, K.; Mihovilovic, M. D. J. Org. Chem., 2005, 70, 567.
36. (a) Nicolaou, K. C; Ritzen, A; Namoto, K; Buey, R. M; Diaz, J. F.; Andreu, J. M.; Wartmann, M; Altmann, K. H; Brate, A; Giannakakou, P. Tetrahedron, 2002, 58, 6413.
37. b) Ganesh, T; Schilling, J. K; Palakodety, R. K; Ravindra, R; Shanker, N; Bane, S; Kingston, D. G. I. Tetrahedron, 2003, 59, 9979.
38. c) Milstein, D.; Stille, J. K. J. Am. Chem. Soc., 1978, 100, 3636.
39. d) Stille, J. K. Angew. Chem. Int. Ed., 1986, 25, 508.
40. e) Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed., 2004, 43, 4704.
41. (a) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem., 2000, 65, 4193.
42. b) Hodgetts, K. J; Kershaw, M. T. Org. Lett., 2002, 4, 1363.
43. c) Hodgetts, K. J; Kershaw, M. T. Org. Lett., 2003, 5, 2911.
44. d)Miyaura, N.; Suzuki, A. J. Chem. Soc. Chem. Commun., 1979, 866-867.
45. e) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett., 1979, 3437.
46. f) Miyaura, N.; Suzuki, A. Chem. Rev., 1995, 95, 2457.
47. Hämmerle, J.; Spina, M; Schnürch, M.; Mihovilovic, M. D.; Stanetty, P. Synthesis, 2008, 3099.