Regio- And stereoselective synthesis of fluoroalkenes by Directed Au(I) catalysis

Organic Letters

Volumn 11, Issue 19, 2009, Pages 4318-4321

  Gorske, Benjamin C ^a   Mbofana, Curren T ^a   Miller, Scott J ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATED HYDROCARBON; ORGANOGOLD COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; STEREOISOMERISM;

EID: 70350180774     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9016782     Document Type: Article

References (24)

1. Cox, J. D.; Gundry, H. A.; Head, A. J. Trans. Faraday Soc. 1964, 60, 653.
2. Bondi, A. J. phys. Chem. 1964, 68, 441.
3. Banks, H. D. J. Org. Chem. 2006, 71, 8089.
4. Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004. 5. 637.
5. (a) Garrett, G. S.; Emge, T. J.; Lee, S. C.; Fischer, E. M.; Dyehouse, K.; Mclver, J. M. J. Org. Chem. 1991, 56, 4823.
6. (b) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107.
7. (c) Otaka, A.; Mitsuyama, E.; Watanabe, J.; Watanabe, H.; Fujii, N. Biapolymers 2004, 76, 140.
8. (d) Urban, J. J.; Tillman, B. G.; Cronin, W. A. J. Phys. Chem. A 2006, 110, 11120.
9. Jakobsche, C. E.; Peris, G.; Miller, S. J. Aneew. Chem., Int. Ed. 2008, 47, 6707.
10. (a) Couve-Bonnaire, S.; Cahard, D.; Pannecoucke, X. Ore. Biomol. Chem. 2007, 5, 1151.
11. (b) Sano, S.; Kuroda, Y.; Saito, K.; Ose, Y.; Nagao, Y. Tetrahedron 2006, 62, 11881.
12. (c) Narumi, T.; Tomita, K.; Inokuchi, E.; Kobayashi, K.; Oishi, S.; Ohno, H.; Fujii, N. Tetrahedron 2008, 64, 4332, and references therein.
13. For recent reviews of Au catalysis in organic chemistry, see (a) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
14. (b) Arcadi, A. Chem. Rev. 2008, 108, 3266.
15. (c) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
16. Akatia, J. A, Bhattacharyya, K. X, Müller, P., Sadighi, J. Am. Chem. Soc. 2007, 129, 7736.
17. (a) Yu. M.; Zhang, G.; Zhang, L. Tetrahedron 2009, 65, 1846.
18. (b) Yu, M.; Zhang, G.; Zhang, L. Org. Lett. 2007, 9, 2147.
19. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
20. (a) Cortea, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Aggew. Chem., Int. Ed. 2008, 47, 718.
21. (b) Mauleón, P.; Krinsky, J. L.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 4513.
22. (c) Marion, N.; Díez-González, S.; de Frémont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 45, 3647.
23. Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763.
24. Au(I)-alkene complexes containing an N-heterocyclic carbene ligand have also been reported; see: Brown, T. J.; Dickens, M. G.; Widenhoefer, R. A. J. Am. Chem. Soc. 2009, 131, 6350, and references therein.