Gold(I) complexes with hydrogen-bond supported heterocyclic carbenes as active catalysts in reactions of 1,6-enynes

Inorganic Chemistry

Volumn 47, Issue 23, 2008, Pages 11391-11397

  Bartolomé, Camino ^a   Ramiro, Zoraida ^a   Pérez Galán, Patricia ^b   Bour, Christophe ^b   Raducan, Mihal ^b   Echavarren, Antonio M ^b   Espinet, Pablo ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57949090972     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic801446v     Document Type: Article

References (50)

1. Bartolomé, C.; Carrasco-Rando, M.; Coco, S.; Cordovilla, C.; Martín-Alvarez, J. M.; Espinet, P. Inorg. Chem. 2008, 47, 1616-1624.
2. Bartolomé, C.; Carrasco-Rando, M.; Coco, S.; Cordovilla, C.; Espinet, P.; Martín-Alvarez, J. M. Dalton Trans. 2007, 5339-5345.
3. Bonati, F.; Burini, A.; Pietroni, B. R.; Bovio, B. J. Organomet. Chem. 1991, 408, 271-280.
4. (a) Hashmi, A. S. J. Chem. Rev. 2007, 107, 3180-3211.
5. (b) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333-346.
6. (c) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449.
7. (d) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395-403.
8. (e) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3265.
9. (f) Gorin, D. J.; Sherry, B. D.; Toste, F. D. 2008, 108, 3351-3378.
10. (g) Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem., Int. Ed. 2008, 47, 4268-4315.
11. (a) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-2406.
12. (b) Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Cárdenas, D. J.; Buñuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146-6148.
13. (c) Nieto-Oberhuber, C.; Muñoz, M. P.; López, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. Eur. J 2006, 12, 1677-1693.
14. (d) Nieto-Oberhuber, C.; Lopez, S.; Jiménez-Núñez, E.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 5916-5923.
15. Cabello, N.; Jiménez-Núñez, E.; Buñuel, E.; Cárdenas, D. J.; Echavarren, A. M. Eur. J. Org. Chem. 2007, 421, 7-4223.
16. Nevado, C.; Ferrer, C.; Echavarren, A. M. Org. Lett. 2004, 6, 3191-3194.
17. (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635.
18. (b) Ferrer, C.; Raducan, M.; Nevado, C.; Claverie, C. K.; Echavarren, A. M. Tetrahedron 2007, 63, 6306-6316.
19. Genin, E.; Leseurre, L.; Toullec, P. Y.; Genêt, J. P.; Michelet, V. Synlett 2007, 1780-1784.
20. Toullec, P. Y.; Genin, E.; Leseurre, L.; Genêt, J.-P.; Michelet, V. Angew. Chem., Int. Ed. 2006, 45, 7427-7430.
21. Amijs, C. H. M.; Ferrer, C.; Echavarren, A. M. Chem. Commun. 2007, 698-700.
22. (a) Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178-6179.
23. (b) Nieto-Oberhuber, C.; Pérez-Galán, P.; Herrero-Gómez, E.; Lauterbach, T.; Rodríguez, C.; López, S.; Bour, C.; Rosellon, A.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269-279.
24. (c) Lemière, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimana, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207-2209.
25. (d) Kim, S. M.; Park, J. H.; Choi, S. Y.; Chung, Y. K. Angew. Chem., Int. Ed. 2007, 46, 6172-6175.
26. (e) Baskar, B.; Bae, H. J.; An, S. E.; Cheong, J. Y.; Rhee, Y. H.; Duschek, A.; Kirsch, S. F. Org. Lett. 2008, 10, 2605-2607.
27. (f) Bae, H. J.; Baskar, B.; An, S. E.; Cheong, J. Y.; Thangadurai, D. T.; Hwang, I.-C.; Rhee, Y. H. Angew. Chem., Int. Ed. 2008, 47, 2263-2266.
28. (g) Fürstner, A.; Morency, L. Angew. Chem. 2008, 120, 5108-5111.
29. (h) Fürstner, A.; Morency, L. Angew. Chem., Int. Ed. 2008, 47, 5030-5033.
30. (a) de Frémont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 2411-2418.
31. (b) Marion, N.; de Frémont, P.; Lemière, G.; Stevens, E. D.; Fensterbank, L.; Malacria, M.; Nolan, S. P. Chem. Commun. 2006, 2048-2050.
32. Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156-5159.
33. Ricard, L.; Gagosz, F. Organometallics 2007, 26, 4704-4707.
34. de Frémont, P.; Stevens, E. D.; Fructos, M. R.; Díaz-Requejo, M. M.; Pérez, P. J.; Nolan, S. P. Chem. Commun. 2006, 2045-2047.
35. Amijs, G H. M.; López-Carrillo, V.; Raducan, M.; Pérez-Galán, P.; Ferrer, C.; Echavarren, A. M. J. Org. Chem. 2008, 73, 7721-7730.
36. Braunstein, P.; Müller, A.; Bögge, H. Inorg. Chem. 1986, 25, 2104-2106.
37. (a) Bovio, B.; Burini, A.; Pietroni, B. R. J. Organomet. Chem. 1993, 452, 287-291.
38. (b) Wang, H. M. J.; Chen, C. Y. L.; Lin, I. J. B. Organometallics 1999, 18, 1216-1227.
39. (a) Balch, A. L.; Olmstead, M. M.; Vickery, J. C. Inorg. Chem. 1999, 38, 3494-3499.
40. (b) Beck, W.; Weigand, W.; Nagel, U.; Schaal, M. Angew. Chem., Int. Ed. 1984, 23, 377-378.
41. (c) Banditelli, G.; Bonati, F.; Calogero, S.; Valle, G.; Wagner, F. E.; Wordel, R. Organometallics 1987, 6, 2019.
42. (d) White-Morris, R. L.; Olmstead, M. M.; Balch, A. L. J. Am. Chem. Soc. 2003, 125, 1033-1040.
43. Pauling L. The Nature of the Chemical Bond, 3rd ed.; Cornell University: Ithaca, NY, 1960; p 282.
44. Hydrogen bonding distance ranges proposed in the literature: strong, 1.2-1.5 Å; moderate, 1.5-2.2 Å; weak, 2.2-3.2 Å: Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
45. Perrin, D. D.; Armarego, W. F. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, U. K., 1988.
46. SMART V5.051 Diffractometer Control Software; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
47. SAINT V6.02 Integration Software; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1999.
48. Sheldrick, G. M. SADABS: A Program for Absorption Correction with the Siemens SMART System; University of Göttingen:Germany, 1996.
49. SHELXTL Program System, Version 5.1; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
50. International Tables for Crystallography; Kluwer: Dordrecht, 1992; Vol. C.