Intramolecular cyclization of ruthenium vinylidene complexes with a tethering vinyl group: Facile cleavage and reconstruction of the C-C double bond

Journal of the American Chemical Society

Volumn 129, Issue 48, 2007, Pages 14974-14980

  Cheng, Cheng Wei ^a   Kuo, Yi Chun ^a   Chang, Shu Hao ^a   Lin, Ying Chih ^a   Liu, Yi Hong ^a   Wang, Yu ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR CYCLIZATION; RUTHENIUM ACETYLIDE COMPLEXES; TETHERING VINYL GROUP;

BOND STRENGTH (CHEMICAL); CYCLIZATION; CYCLOADDITION; METAL COMPLEXES; X RAY DIFFRACTION ANALYSIS;

RUTHENIUM COMPOUNDS;

5 ALKOXY 3,3 DIPHENYLCYCLOHEX 1 ENE; 5 ETHOXY 3,3 DIPHENYLCYCLOHEX 1 ENE; 5 ISOPROPOXY 3,3 DIPHENYLCYCLOHEX 1 ENE; 5 METHOXY 3,3 DIPHENYLCYCLOHEX 1 ENE; ALKENE DERIVATIVE; CARBENOID; CARBON 13; DEUTERIUM; ETHER; METHANOL; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; X RAY DIFFRACTION;

EID: 36949001332     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074951p     Document Type: Article

References (40)

1. (a) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
2. (b) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
3. (c) Méndez, M.; Muńoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
4. (d) Martín-Matute, B.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757.
5. (e) Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200.
6. (f) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
7. (a) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
8. (b) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
9. (c) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J. P. Chem. Commun. 2004, 850.
10. (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
11. (b) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
12. (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
13. (d) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704.
14. (a) Driver, S. T.; Geissert, A. J. Chem. Rev. 2004, 104, 1317.
15. (b) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627.
16. (a) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
17. (b) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouries, V.; Dhimane, A. L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
18. (c) Nieto-Oberhuber, C.; Muñoz, M. P.; Buńuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
19. (a) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts: Org. Chem. 2003, 16, 397.
20. (b) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
21. (c) Nieto-Oberhuber, C.; López, S.; Jiménez- Núñez, E.; Echavarren, A. M. Chem.-Eur. J. 2006, 12, 5916.
22. (d) Echavarren, A. M.; Nevadoa, C. Chem. Soc. Rev. 2004, 33, 431.
23. Yen, Y. S.; Huang, S. L.; Liu, Y. H.; Sung, H. L.; Wang, Y.; Lin, Y. C. J. Am. Chem. Soc. 2005, 127, 18037.
24. Selegue, J. P. Organometallics 1982, 1, 217.
25. (a) Esteruelas, M. A.; Gómez, A.; López, A. M.; Modrego, J.; Oñate, E. Organometallics 1997, 16, 5826.
26. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S.; Pérez-Carrenõ, E. Organometallics 1996, 15, 2137.
27. 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.
28. Buzas, A. K.; Istrate, F. M.; Gagosz, F. Angew. Chem., Int. Ed. 2007, 46, 1141.
29. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
30. Sun, J.; Conley, M. P.; Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2006, 128, 9705.
31. (a) Alvarez, P.; Lastra, E.; Gimeno, J.; Bassetti, M.; Falvello, L. R. J. Am. Chem. Soc. 2003, 125, 2386.
32. (b) Braña, P.; Gimeno, J.; Sordo, J. A. J. Org. Chem. 2004, 69, 2544.
33. Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
34. Cadierno, V.; Conejero, S.; Díez, J.; Gamasa, M. P.; Gimeno, J.; García-Granda, S. Chem. Commun. 2003, 840.
35. Odedra, A.; Wu, C. J.; Pratap, T. B.; Huang, C. W.; Ran, Y. F.; Liu, R. S. J. Am. Chem. Soc. 2005, 127, 3406.
36. (a) Bruce, M. I.; Wallis, R. C. Aust. J. Chem. 1979, 32, 1471.
37. (b) Joslin, F. L.; Mague, J. T.; Roundhill, D. M. Organometallics 1991, 10, 521.
38. (c) Oshima, N.; Suzuki, H.; Moro-Oka, Y. Chem. Lett. 1984, 1161.
39. The SADABS program is based on the method of Blessing, see: Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33.
40. SHELXTL: Structure Analysis Program, version 5.04; Siemens Industrial Automation Inc.: Madison, WI, 1995.