Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles

Journal of the American Chemical Society

Volumn 130, Issue 10, 2008, Pages 2926-2927

  Lebrasseur, Nathalie ^a   Larrosa, Igor ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PALLADIUM; PHOSPHINE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ROOM TEMPERATURE;

CATALYSIS; INDOLES; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES; STEREOISOMERISM; TEMPERATURE;

EID: 41449108490     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710731a     Document Type: Article

References (36)

1. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
2. (b) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 20, 35.
3. (c) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
4. (d) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev 2007, 36, 1173.
5. (e) Godula, K.; Sames, D. Science 2006, 312, 67.
6. (f) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
7. (a) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
8. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Shulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
9. (c) Anastasia, L.; Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
10. (a) Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924.
11. (b) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
12. (a) Wang, X.; Gribkov, D. V.; Sames, D. J. Org. Chem. 2007, 72, 1476.
13. (b) Zhang, Z.; Hu, Z.; Yu, Z.; Lei, P.; Chi, H.; Wang, Y.; He, R. Tetrahedron Lett. 2007, 48, 2415.
14. (c) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 1970.
15. (d) Touré, B. B.; Lane, B. S.; Sames, D. Org. Lett. 2006, 8, 1979.
16. (e) Bellina, F.; Cauteruccio, S.; Rossi, R. Eur. J. Org. Chem. 2006, 1379.
17. (f) Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
18. (g) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
19. (h) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 4990.
20. (i) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
21. For recent C-arylation of indoles with unactivated arenes see: (a) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072.
22. (b) Stuart, D. R.; Fagnou, K. Science 2007, 317, 1172.
23. (c) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
24. (a) Liston, D. J.; Lee, Y. J.; Scheidt, W. R.; Reed, C. A. J. Am. Chem. Soc. 1989, 111, 6643.
25. (b) Albano, V. G.; Di Serio, M.; Monari, M.; Orabona, I.; Panunzi, A.; Ruffo, F. Inorg. Chem. 2002, 41, 2672.
26. (a) Nova, A.; Ujaque, G.; Maseras, F.; Lledos, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571.
27. (b) Amatore, C.; Carre, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics, 1995, 14, 5605.
28. (a) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
29. (b) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
30. For a mechanistic discussion on C-2/C-3 selectivity in indole arylation, see ref 4g
31. Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879 and references therein.
32. (a) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342.
33. (b) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896.
34. 3CN (14%), AcOH (50%), and DMA (50%) compared to DMF (95%).
35. (a) Amatore, C.; Jutand, A.; Lemaitre, F.; Ricard, J. L.; Kozuch, S.; Shaik, S. J. Organomet. Chem. 2004, 689, 3728.
36. (b) Schmulling, M.; Grove, D. M.; van Koten, G.; van Eldik, R.; Veldman, N.; Spek, A. L. Organometallics 1996, 15, 1384.