Palladium-Catalyzed C-H Homocoupling of Thiophenes: Facile Construction of Bithiophene Structure

Journal of the American Chemical Society

Volumn 126, Issue 16, 2004, Pages 5074-5075

  Masui, Kentaro ^a   Ikegami, Haruka ^a   Mori, Atsunori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BITHIOPHENE; PALLADIUM; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; HALOGENATION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 1942521272     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031855p     Document Type: Article

References (26)

1. (a) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
2. (b) Mochizuki, H.; Hasui, T.; Kawamoto, M.; Shiono, T.; Ikeda, T.; Adachi, C.; Taniguchi, Y.; Shirota, T. Chem. Commun. 2000, 1923.
3. (c) Dölling, K.; Zaschke, H.; Schubert, H. J. Prakt. Chem. 1979, 321, 643.
4. (a) Briehn, C. A.; Schiedel, M.-S.; Bonsen, E. M.; Schumann, W.; Bäuerle, P. Angew. Chem., Int. Ed. 2001, 40, 4680.
5. (b) Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Katz, H. E.; Marks, T. J. Angew. Chem., Int. Ed. 2003, 42, 3900.
6. (c) Yamamoto, T.; Arai, M.; Kokubo, H.; Sasaki, S. Macromolecules 2003, 36, 7986.
7. (a) Tour, J. M. Chem. Rev. 1996, 96, 537.
8. (b) Wei, Y.; Wang, B.; Tian, J. Tetrahedron Lett. 1995, 36, 665.
9. (c) Parrish, J. P.; Jung, Y. C.; Floyd, R. J.; Jung, W. Tetrahedron Lett. 2002, 43, 7899.
10. (d) Hassan, J.; Gozzi, C.; Lemaire, M. C. R. Acad. Sci., Ser. 11c: Chim. 2000, 3, 517.
11. (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
12. (b) Yokooji, A.; Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2003, 59, 5685.
13. (c) Kondo, Y.; Komine, T. Sakamoto, T. Org. Lett. 2000, 2, 3111.
14. (d) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274.
15. (e) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 10580.
16. (f) Sezen, B.; Sames, D. Org. Lett. 2003, 5, 3607.
17. (g) Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
18. (h) Kamigata, N. Yoshikawa, M. Shimizu, T. J. Fluorine Chem. 1998, 87, 91.
19. For a review: (i) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
20. 2 is shown to take place much less efficiently: Itahara, T.; Hashimoto, M.; Yumisashi, H. Synthesis 1984, 255.
21. Yields of 2a were 54, 24, and <4%, respectively, when 1.0, 0.5, and 0.05 equiv of AgF were employed for the homocoupling reaction.
22. See Supporting Information.
23. 3N, which also effected homocoupling of 1a in 51% yield, showed the ccorresponding signal at -152.1 ppm.
24. 19F NMR. McCarthy, J. R.; Peet, N. P. ; LeTourneau, M. E.; Inbasekaran, M. J. Am. Chem. Soc. 1985, 107, 735.
25. This cross-coupling reaction was found to occur with several thiophene and thiazole derivatives also. Details will be described in due course.
26. Albers, W. M.; Canters, G. W.; Reedijk, J. Tetrahedron 1995, 51, 3895.