Facile synthesis of 2,5-diarylthiazoles via palladium-catalyzed tandem C-H substitutions. Design of tunable light emission and liquid crystalline characteristics

Journal of the American Chemical Society

Volumn 125, Issue 7, 2003, Pages 1700-1701

  Mori, Atsunori ^a   Sekiguchi, Akitoshi ^a   Masui, Kentaro ^a   Shimada, Tomohiro ^a   Horie, Masaki ^a   Osakada, Kohtaro ^a   Kawamoto, Masuki ^a   Ikeda, Tomiki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; THIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; LIGHT; LIQUID CRYSTAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0037442583     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0289189     Document Type: Article

References (33)

1. (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
2. (b) Weissman, H.; Song, X.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337.
3. (c) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
4. (d) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
5. (e) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
6. (f) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
7. (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
8. (h) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
9. (i) Waltz, K. M.; Hartwig, J. F. Science 1997, 277, 211.
10. (j) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305.
11. (a) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
12. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
13. (a) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402-428.
14. (b) Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121-128,
15. (c) Shirota, Y. J. Mater. Chem. 2000, 10, 1-25.
16. (d) Kim, D. Y.; Cho, H. N.; Kim, C. Y. Prog. Polym. Sci. 2000, 25, 1089-1139.
17. (e) Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471-1507.
18. (a) Demus, D.; Goodby, J. W.; Gray, G. W.; Spiess, H.-W. Handbook of Liquid Crystals; Wiley: Germany, 1998.
19. (b) Bahadur, B. Liquid Crystals-Applications and Uses; World Scientific: Singapore, 1990.
20. (a) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649.
21. (b) Mori, A.; Kawashima, J.; Shimada, T.; Suguro, M.; Hirabayashi, K.; Nishihara, Y. Org. Lett. 2000, 2, 2935.
22. (c) Mori, A.; Kondo, T.; Kato, T.; Nishihara, Y. Chem, Lett. 2001, 286.
23. The reaction at 40 °C for 96 h afforded 61% of 3a (3a/4a = 9: 1) and at room temperature for 96 h, 35% (3a/4a = 20:1).
24. Dölling, K.; Zaschke, H.; Schubert, H. J. Prakt. Chem. 1979, 321, 643.
25. An example of library construction for light-emitting materials: Shiedel, M.-S.; Briehn, C. A.; Bäuerle, P. Angew. Chem., Int. Ed. 2001, 40, 4677.
26. Mochizuki, H.; Hasui, T.; Kawamoto, M.; Shiono, T.; Ikeda, T.; Adachi, C.; Taniguchi, Y.; Shirota, T. Chem. Commun. 2000, 1923.
27. Kaifer, A. E.; Gémez-Kaifer, M. Supramolecular Electrochemistry; Wiley-VCH: Weinheim, 1999.
28. Tables of peak potential values for 3 and 6: See the Supporting Information.
29. (a) Kido, J.; Kohda, M.; Okuyama, K.; Nagai, K. Appl. Phys. Lett. 1992, 61, 761-763.
30. (b) Zhang, C.; von Seggern, H.; Kraabel, B.; Schmidt, H.-W.; Heeger, A. J. Synth. Met. 1995, 72, 185-188.
31. (c) Kido, J.; Shionoya, H.; Nagai, K. Appl. Phys. Lett. 1995, 67, 2281-2283.
32. (d) Birgerson, J.; Kaeriyama, K.; Barta, P.; Bröms, P.; Fahlman, M.; Granlund, T.; Salaneck, W. R. Adv. Mater. 1996, 8, 982-985.
33. (e) Wu, C. C.; Sturm, J. C.; Register, R. A.; Tian, J.; Dana, E. P.; Thompson, M. E. IEEE Trans. Electron Devices 1997, 44, 1269-1281.