Pd-catalyzed β-selective direct C-H bond arylation of thiophenes with aryltrimethylsilanes

Organic Letters

Volumn 14, Issue 24, 2012, Pages 6186-6189

  Funaki, Kenji ^a   Sato, Tetsuo ^a   Oi, Shuichi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIOPHENE; COPPER; CUPRIC CHLORIDE; PALLADIUM; SILANE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; MOLECULAR STRUCTURE; PALLADIUM; SILANES; THIOPHENES;

EID: 84871606646     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3029109     Document Type: Article

References (34)

1. Cross-Coupling Reactions: A Practical Guide in Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002.
2. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
3. Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200
4. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
5. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
6. Roger, J.; Gottumukkala, A. L.; Doucet, H. ChemCatChem 2010, 2, 20
7. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467
8. Kondo, S.; Komine, T.; Sakamoto, T. Org. Lett. 2000, 2, 3111
9. Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. Eur. J. Org. Chem. 2006, 3, 693
10. Gorelsky, S. I. Organometallics 2012, 31, 794
11. Ohta, A.; Akita, Y.; Ohkuwa, T.; Chiba, M.; Fukunaga, R.; Miyafuji, A.; Nakata, T.; Tani, N.; Aoyagi, Y. Heterocycles 1990, 31, 1951
12. Gozzi, C.; Lavenot, L.; Ilg, K.; Penalva, V.; Lemaire, M. Tetrahedron Lett. 1997, 38, 8867
13. Kobayashi, K.; Sugie, A.; Takahashi, M.; Masui, K.; Mori, A. Org. Lett. 2005, 7, 5083
14. Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748
15. Join, B.; Yamamoto, T.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 3644
16. Yanagisawa, S.; Itami, K. Tetrahedron 2011, 67, 4425
17. Liegault, B.; Petrov, I.; Gorelsky, S. I.; Fagnou, K. J. Org. Chem. 2010, 75, 1047
18. Schnapperelle, I.; Breitenlechner, S.; Bach, T. Org. Lett. 2011, 13, 3640
19. Yanagisawa, S.; Ueda, K.; Sekizawa, H.; Itami, K. J. Am. Chem. Soc. 2009, 131, 14622
20. Ueda, K.; Yanagisawa, S.; Yamaguchi, J.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 8946
21. Kirchberg, S.; Tani, S.; Ueda, K.; Yamaguchi, J.; Studer, A.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 2387
22. Kawai, H.; Kobayashi, Y.; Oi, S.; Inoue, Y. Chem. Commun. 2008, 1464
23. Funaki, K.; Kawai, H.; Sato, T.; Oi, S. Chem. Lett. 2011, 40, 1050
24. Ball, L. T.; Lloyd-Jones, G. C.; Russell, C. A. Science 2012, 337, 1644
25. Shibata, K.; Miyazawa, K.; Goto, Y. Chem. Commun. 1997, 1309
26. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684
27. Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053
28. Fu, G. C.; Lee, J.-Y. J. Am. Chem. Soc. 2003, 125, 5616
29. Seganish, W. M.; DeShong, P. J. Org. Chem. 2004, 69, 6790
30. Eaborn, C. J. Organomet. Chem. 1975, 100, 43
31. Valk, J.-M.; Boersma, J.; van Koten, G. J. Organomet. Chem. 1994, 483, 213
32. Steenwinkel, P.; Gossage, R. A.; Maunula, T.; Grove, D. M.; van Koten, G. Chem.-Eur. J. 1998, 4, 763
33. Rauf, W.; Brown, J. M. Synlett 2009, 19, 3103
34. Steinmetz, M.; Ueda, K.; Grimme, S.; Yamaguchi, J.; Kirchberg, S.; Itami, K.; Studer, A. Chem.-Asian J. 2012, 7, 1256