Intermolecular cross-coupling of simple arenes via C-H activation by tuning concentrations of arenes and TFA

Organometallics

Volumn 25, Issue 26, 2006, Pages 5973-5975

  Li, Ruoshi ^a   Jiang, Li ^a   Lu, Wenjun ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL BONDS; OLEFINS; TUNING;

ARENES; CATALYTIC SYSTEMS; INTERMOLECULAR CROSS COUPLING; UNSYMMETRICAL BIARYLS;

ORGANOMETALLICS;

EID: 33846396118     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060889d     Document Type: Article

References (31)

1. Metal-Catalyzed Cross-Coupling Reactions; Dieterich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
2. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
3. (a) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050 and references therein.
4. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
5. (c) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
6. (d) Wakui, H.; Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2004, 126, 8658.
7. (e) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
8. (f) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
9. (g) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
10. (h) Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669.
11. Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
12. (j) Glover, B.; Harvey. K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301.
13. (a) Mukhopadhyay, S.; Rothenberg, G.; Lando, G.; Agbaria, K.; Kazanci, M.; Sasson, Y. Adv. Synth. Catal. 2001, 343, 455.
14. (b) Okamoto, M.; Yamaji, T. Chem. Lett. 2001, 212.
15. (c) Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074.
16. (d) Mulrooney, C. A.; Li, X.; DiVirgilio, E. S.; Kozlowski, M. C. J. Am. Chem. Soc. 2003, 125, 6856.
17. (e) Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500.
18. (f) Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137.
19. (a) VanHelden, R.; Verberg, G. Recl. Trav. Chim. Pays-Bas 1965, 84, 1263.
20. (b) Fujiwara, Y.; Moritani, I.; Ikegami, K.: Tanaka, R.; Teranishi, S. Bull. Chem. Soc. Jpn. 1970, 43, 863.
21. (a) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
22. (b) Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
23. (c) Lu, W.; Jia, C.; Kitamura, T.; Fujiwara, Y. Org. Lett. 2000, 2, 2927.
24. (d) Taniguchi, Y.; Yamaoka, Y.; Nakata, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1995, 345.
25. (e) Lu, W.; Yamaoka, Y.; Taniguchi, Y.; Kitamura, T.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1999, 550, 290.
26. (f) Shibahara, F.; Kinoshita, S.; Nozaki, K. Org. Lett. 2004, 6, 2437.
27. (a) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
28. (b) Ackerman, L. J.; Sadighi, J. P.; Kurtz, D. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2003, 22, 3884.
29. (c) Konze, W. V.; Scott, B. L.; Kubas, G. J. J. Am. Chem. Soc. 2002, 124, 12550
30. 8. See the Supporting Information.
31. Tunge, J. A.; Foresee, L. N. Organometallics 2005, 24, 6440.