Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides

Organic Letters

Volumn 9, Issue 8, 2007, Pages 1449-1451

  Chiong, Hendrich A ^a   Daugulis, Olafs ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247489285     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0702324     Document Type: Article

References (34)

1. Reviews: (a) Suzuki, A. Chem. Commun. 2005, 4759.
2. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
3. (c) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201.
4. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263.
5. Reviews: (a) Miura, M.: Nomura, M. Top. Curr. Chem. 2002, 219, 211.
6. (b) Kakiuchi, F.; Chatani, N. Adv. Svnth. Catal. 2003, 345, 1077.
7. (c) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
8. (d) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
9. (a) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327.
10. (b) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.: Gohma, K.; Komatsu, J.: Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257.
11. (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
12. (b) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
13. (c) Lavenot, L.; Gozzi, C.; Ilg, K.; Orlova, I.; Penalva, V.; Lemaire, M. J. Organomet. Chem. 1998, 567, 49.
14. (d) Yokooji, A.; Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2003, 59, 5685.
15. (e) McClure, S. M.; Glover, B.; McSorley, E.; Millar, A.; Osterhout, M. H.; Roschangar, F. Org. Lett. 2001, 3, 1677.
16. (f) Rieth, R. D.; Mankad, N. P.; Calimano, E.; Sadighi, J. P. Org. Lett. 2004, 6, 3981.
17. (g) Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. J. Org. Chem. 2005, 70, 3997.
18. (h) Čerňa, L.; Pohl, R.; Klepetářová, B.; Hocek, M. Org. Lett. 2006, 8, 5389.
19. (i) Parisien, M.; Valette, D.; Fagnou, K. J. Org. Chem. 2005, 70, 7578.
20. (j) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
21. (k) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
22. (l) Bellina, F.; Cauteruccio, S.; Rossi, R. Eur. J. Org. Chem. 2006, 1379.
23. (m) Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350.
24. (n) Bowie, A. L., Jr.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207.
25. (o) Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
26. (p) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
27. Use of aryl chlorides in pyrazine oxide arylation: (q) Leclerc, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
28. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4177.
29. Ehrentraut, A.; Zapf, A.; Beller, M. Synlett 2000, 1589.
30. Jacobson, K. A.; Shi, D.; Gallo-Rodriguez, C.; Manning, M., Jr.; Müller, C.; Daly, J. W.; Neumeyer, J. L.; Kiriasis, L.; Pfleiderer, W. J. Med. Chem. 1993, 36, 2639.
31. Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523.
32. (a) Zollinger, H. Adv. Phys. Org. Chem. 1964, 2, 163. An electrophilic substitution mechanism was proposed for the arylation of indoles.
33. (b) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
34. Gupta, R. R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry II; Springer Publishing: New York, 1999; p 388.