Catalytic intermolecular direct arylation of perfluorobenzenes

Journal of the American Chemical Society

Volumn 128, Issue 27, 2006, Pages 8754-8756

  Lafrance, Marc ^a   Rowley, Christopher N ^a   Woo, Tom K ^a   Fagnou, Keith ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; N,N DIMETHYLACETAMIDE; PERFLUORO COMPOUND; POTASSIUM CARBONATE; TOLUENE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; REACTION ANALYSIS; REACTION TIME;

EID: 33745959757     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062509l     Document Type: Article

References (38)

1. For reviews, see: (a) Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
2. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
3. (c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
4. (d) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
5. (e) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
6. For a review, see: Campeau, L. C.; Fagnou, K. Chem. Commun. 2006, 1253.
7. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
8. For example, see: (a) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
9. (b) Park, C. H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
10. For an alternate mechanism involving carbene intermediates, see: Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
11. Electron-rich hcterocyclic arenes have been successfully employed. For example, see: (a) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
12. (b) Li, W. J.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Javadi, G. J.; Cai, D.; Larsen, R. D. Org. Lett. 2003, 5, 4835.
13. (c) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
14. (d) Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
15. For example, see: (a) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
16. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
17. (c) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
18. (d) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
19. Intramolecular direct arylation reactions have also been reported. For example, see: (a) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K.; J. Am. Chem. Soc., 2004, 126, 9186.
20. (b) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
21. (c) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
22. (d) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
23. (a) Zahn, A.; Brotschi, C.; Leumann, C. Chem.-Eur. J. 2005, 11, 2125.
24. (b) Russell, M. G. N.; et al. J. Med. Chem. 2005, 48, 1367.
25. Sakamoto, Y.; Suzuki, T.; Miura, A.; Fujikawa, H.; Tokito, S.; Taga, Y. J. Am. Chem. Soc. 2000, 122, 1832.
26. (a) Hwang, D. H.; Song, S. Y.; Ahn, T.; Chu, H. Y.; Do, L. M.; Kim, S. H.; Shim, H. K.; Zyung, T. Synth. Met. 2000, 111, 485.
27. (b) Montes, V. A.; Li, G.; Pohl, R.; Shinar, J.; Anzenbacher, P. Adv. Mater. 2004, 16, 2001.
28. (c) Tsuzuki, T.; Shirasawa, N.; Suzuki, T.; Tokito, S. Adv. Mater. 2003, 15, 1455.
29. Kitamura, T.; Wada, Y.; Yanagida, S. J. Fluor. Chem. 2000, 105, 305.
30. (a) Weck, M.; Dunn, A. R.; Matsumoto, K.; Coates, G. W.; Lobkovsky, E. B.; Grubbs, R. H. Angew. Chem., Int. Ed. 1999, 38, 2741.
31. (b) Nitschke, J. R.; Tilley, T. D. J. Am. Chem. Soc. 2001, 123, 10183.
32. 4 salt renders the phosphine ligand air- and bench-stable until it becomes deprotonated by the action of base under the reaction conditions. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
33. Schlosser, M.; Marzi, E. Chem.-Eur. J. 2005, 11, 3449.
34. For experimental details, see the Supporting Information.
35. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
36. (b) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
37. 17 density functional theory calculations were performed with the Jaguar 6.0 package with the LACV2P* basis set and pseudopotential combination of Jaguar. Full details are provided in the Supporting Information.
38. A full account of the mechanisms explored computationally is detailed in the Supporting Information.