Divergent mechanisms for the skeletal rearrangement and [2+2] cycloaddition of enynes catalyzed by gold

Angewandte Chemie - International Edition

Volumn 44, Issue 38, 2005, Pages 6146-6148

  Nieto Oberhuber, Cristina ^a,b   López, Salomé ^a   Muñoz, M Paz ^b   Cárdenas, Diego J ^b   Buñuel, Elena ^b   Nevado, Cristina ^b   Echavarren, Antonio M ^a,b  

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

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Alkynes; Cyclization; Density functional calculations; Gold; Rearrangement

Indexed keywords

BUTENES; GOLD; ORGANOMETALLICS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

ALKYNES; CYCLIZATION; DENSITY FUNCTIONAL CALCULATIONS; REARRANGEMENT;

AROMATIC COMPOUNDS;

EID: 25844453872     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501937     Document Type: Article

References (34)

1. Reviews: a) G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215-236;
2. b) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
3. c) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382;
4. d) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436.
5. a) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10 511-10 520;
6. b) C. Nevado, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2003, 9, 2627-2635;
7. c) M. P. Muñoz, J. Adrio, J. C. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300.
8. S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709.
9. a) B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1988, 110, 1636-1638;
10. b) B. M. Trost, M. K. Trost, Tetrahedron Lett. 1991, 32, 3647-3650;
11. c) B. M. Trost, M. Yanai, K. Hoogsteed, J. Am. Chem. Soc. 1993, 115, 5294-5295;
12. d) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11 863-11 869;
13. e) N. Chatani, H. Inoue, T. Kotsuma, S. Murai, J. Am. Chem. Soc. 2002, 124, 10 294-10 295;
14. f) F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509-1511;
15. g) G. B. Bajracharya, I. Nakamura, Y. Yamamoto, J. Org. Chem. 2005, 70, 892-897.
16. For formation of a different type of cyclobutene, see: a) A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245;
17. b) see also ref. [7b].
18. E. Soriano, P. Ballesteros, J. Marco-Contelles, Organometallics 2005, 24, 3172-3181.
19. a) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
20. Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
21. b) C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
22. a) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655;
23. b) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 11 806-11 807;
24. c) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10 858-10 859.
25. a) N. Chatani, H. Inoue, T. Morimoto, T. Muto, S. Murai, J. Org. Chem. 2001, 66, 4433-4436;
26. b) C. H. Oh, S. Y. Bang, C. Y. Rhim, Bull Korean Chem. Soc. 2003, 24, 887-888.
27. P. N. Dickson, A. Wehrli, G. Geier, Inorg. Chem. 1988, 27, 2921-2925.
28. P. S. Lee, S. Sakai, P. Hörstermann, W. R. Roth, E. A. Kallel, K. N. Houk, J. Am. Chem. Soc. 2003, 125, 5839-5848.
29. W. F. Maier, P. von R. Schleyer, J. Am. Chem. Soc. 1981, 103, 1891-1900.
30. G. Oba, G. Moreira, G. Manuel, M. Koenig, J. Organomet. Chem. 2002, 643-644, 324-330.
31. Calculations at the B3LYP/6-31G(d) (C,H,P), LANL2DZ (Au) level.
32. 2 has been shown to take place at 120°C in acetonitrile: G. B. Bajracharya, I. Nakamura, Y. Yamamoto, J. Org. Chem. 2005, 70, 892-897.
33. D. J. Tantillo, R. Hoffmann, J. Am. Chem. Soc. 2001, 123, 9855-9859.
34. -1 more stable than 25 (PM3 calculation).