Phosphine gold(I) bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4133-4136

  Mézailles, Nicolas ^a   Ricard, Louis ^a   Gagosz, Fabien ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25444522675     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0515917     Document Type: Article

References (26)

1. (a) Nieto-Oberhuber, C.; Lopez, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178-6179.
2. (b) Muñoz, M.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometalics 2005, 24, 1293-1300.
3. (c) Nevado, C.; Echavarren, A. M. Chem. Eur. J. 2005, 11, 3155-3164.
4. (d) Nieto-Oberhuber, C.; Muñoz, M.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-2406.
5. (e) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802-5803.
6. (f) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858-10859.
7. (g) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978-15979.
8. (h) Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350-5352.
9. Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
10. (j) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 11806-11807.
11. (k) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962-6963.
12. For a review of Au-catalyzed reactions, see: Hashmi, A. S. K. Gold Bull. 2004, 37, 51-65.
13. Protonation of an alkylgold(I) complex with a strong acid may also be used to generate the cationic species; however, these conditions are not always compatible with the substrates.
14. n can act as an oxidizing agent and thus cause unwanted side reactions. See: Raabe, I.; Krossing, I. Angew. Chem., Int. Ed. 2004, 43, 2066-2090.
15. Raabe, I.; Krossing, I. Chem. Eur. J. 2004, 10, 5017-5030.
16. 3)AuCl and the corresponding silver salt showed their instability. All attempts to isolate these complexes failed.
17. Gagosz, F. Org. Lett. 2005, 7, 4129-4132.
18. Numerous metal triflimides are known as strong Lewis acid catalysts: For lanthanides, see: (a) Ishihara, K., Kubota, M.; Yamamoto, H. Synlett 1996, 265-266 and 839-841.
19. For silicium, see: (b) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226.
20. For tin, see: (c) Vij, A.; Wilson, W. W.; Vij, V.; Corley, C. R.; Tham, F. S.; Gerken, M.; Haiges, R.; Schneider, S.; Schroer, T.; Wagner, R. I. Inorg. Chem. 2004, 43, 3189-3199.
21. For other metals, see: (d) Sibi, M. P.; Petrovic, G. Tetrahedron: Asymmetry 2003, 14, 2879-2882.
22. 6b
23. 6.
24. 3.
25. 3CN, THF, MeOH, ether, toluene...). The crystal structure of 1a was established by X-ray diffraction (CCDC 273834); see Supporting Information.
26. 1b-e, which are all air-stable compounds, were synthesized as described for 1a.