Formation of osmium- and ruthenium-cyclobutylidene complexes by ring expansion of alkylidenecyclopropanes

Journal of the American Chemical Society

Volumn 131, Issue 43, 2009, Pages 15572-15573

  Castro Rodrigo, Ruth ^a   Esteruelas, Miguel A ^a   Fuertes, Sara ^a   López, Ana M ^a   López, Fernando ^c   Mascareñas, José L ^b   Mozo, Silvia ^a   Oñate, Enrique ^a   Saya, Lucía ^b   Villarino, Lara ^b  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENECYCLOPROPANES; CARBON ATOMS; CHEMICAL EQUATIONS; CYCLOBUTYLIDENE; METHYLENECYCLOPROPANES; RING EXPANSION; RING-EXPANSION REACTION; TERMINAL CARBON ATOMS; THREE-MEMBERED RINGS;

CHELATION; OSMIUM; RUTHENIUM; RUTHENIUM COMPOUNDS;

COORDINATION REACTIONS;

BENZYLIDENECYCLOPROPANE; CYCLOBUTANE DERIVATIVE; CYCLOBUTYLIDENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; OSMIUM; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; X RAY DIFFRACTION;

EID: 70350656079     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904893j     Document Type: Article

References (44)

1. Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
2. (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
3. (b) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
4. (a) Lautens, M.; Klute, W.; Tan, W. Chem. Rev. 1996, 96, 49.
5. (b) Gulías, M.; Durán, J.; López, F.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2007, 129, 11026.
6. (c) García-Fandiño, R.; Gulías, M.; Castedo, L.; Granja, J. R.; Mascareñas, J. L.; Cárdenas, D. J. Chem. - Eur. J. 2008, 14, 272.
7. Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111.
8. Fürstner, A.; Aïssa, C. J. Am. Chem. Soc. 2006, 128, 6306.
9. Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc. 2006, 128, 7430.
10. Tian, G.-Q.; Yuan, Z.-L.; Zhu, Z.-B.; Shi, M. Chem. Commun. 2008, 2668.
11. (a) Green, M.; Howard, J. A. K.; Hughes, R. P.; Kellet, S. C.; Woodward, P. J. Chem. Soc., Dalton Trans. 1975, 2007.
12. (b) Osakada, K.; Takimoto, H.; Yamamoto, T. Organometallics 1998, 17, 4532.
13. (c) Osakada, K.; Takimoto, H.; Yamamoto, T. J. Chem. Soc., Dalton Trans. 1999, 853.
14. (d) Nishihara, Y.; Yoda, C.; Osakada, K. Organometallics 2001, 20, 2124.
15. (e) Kozhushkov, S. I.; Foerstner, J.; Kakoschke, A.; Stellfeldt, D.; Yong, L.; Wartchow, R.; de Meijere, A.; Butenschön, H. Chem. - Eur. J. 2006, 12, 5642.
16. Binger, P.; Müller, P.; Podubrin, S.; Albus, S.; Krüger, C. J. Organomet. Chem. 2002, 656, 288.
17. (a) Noyori, R.; Nishimura, T.; Takaya, H. Chem. Commun. 1969, 89.
18. (b) Pinhas, A. R.; Samuelson, A. G.; Risemberg, R.; Arnold, E. V.; Clardy, J.; Carpenter, B. K. J. Am. Chem. Soc. 1981, 103, 1668.
19. (c) Allen, S. R.; Barnes, S. G.; Green, M.; Moran, G.; Trollope, L.; Murrall, N. W.; Welch, A. J.; Sharaiha, D. M. J. Chem. Soc., Dalton Trans. 1984, 1157.
20. (d) Tantillo, D. J.; Carpenter, B. K.; Hoffmann, R. Organometallics 2001, 20, 4562.
21. Mashima, K.; Takaya, H. Organometallics 1985, 4, 1464.
22. See for example:(a) Bolaño, T.; Castarlenas, R.; Esteruelas, M. A.; Modrego, F. J.; Oñate, E. J. Am. Chem. Soc. 2005, 127, 11184.
23. (b) Bolaño, T.; Castarlenas, R.; Esteruelas, M. A.; Oñate, E. J. Am. Chem. Soc. 2007, 129, 8850.
24. (c) Castro-Rodrigo, R.; Esteruelas, M. A.; López, A. M.; Oñate, E. Organometallics 2008, 27, 3547.
25. (a) Caulton, K. G. J. Organomet. Chem. 2001, 617-618, 56.
26. (b) Esteruelas, M. A.; López, A. M.; Oliván, M. Coord. Chem. Rev. 2007, 251, 795.
27. (c) Jia, G. Coord. Chem. Rev. 2007, 251, 2167.
28. (a) Alvarez, P.; Lastra, E.; Gimeno, J.; Bassetti, M.; Falvello, L. R. J. Am. Chem. Soc. 2003, 125, 2386.
29. (b) Díez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E.; Villar, A. Organometallics 2005, 24, 1410.
30. (c) Díez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E.; Villar, A. J. Organomet. Chem. 2006, 691, 4092.
31. See for example:(a) Bohanna, C.; Esteruelas, M. A.; Gómez, A. V.; López, A. M.; Martinez, M.-P. Organometallics 1997, 16, 4464.
32. (b) Tellers, D. M.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 954.
33. (c) Tellers, D. M.; Bergman, R. G. Organometallics 2001, 20, 4819.
34. (d) Bergman, R. G.; Cundari, T. R.; Gillespie, A. M.; Gunnoe, T. B.; Harman, W. D.; Klinckman, T. R.; Temple, M. D.; White, D. P. Organometallics 2003, 22, 2331.
35. (e) Castro-Rodrigo, R.; Esteruelas, M. A.; López, A.M.; Oliván, M.; Oñate, E. Organometallics 2007, 26, 4498.
36. (a) We have not observed products arising from oxidative addition at the cyclopropyl ring, as has been proposed as the first step for Pd-catalyzed transformation of alkylidenecyclopropanes. See ref 3c. (b) 1-Metalla-2- azacyclopent-3-ene complexes are known for group 4 metals. See for example: Thomas, D.; Baumann, W.; Spannenberg, A.; Kempe, R.; Rosenthal, U. Organometallics 1998, 17, 2096.
37. (a) Jia, G.; Meek, D. W.; Gallucci, J. C. Organometallics 1990, 9, 2549.
38. (b) Esteruelas, M. A.; García, M. P.; López, A. M.; Oro, L. A.; Ruiz, N.; Schlünken, C.; Valero, C.; Werner, H. Inorg. Chem. 1992, 31, 5580.
39. (c) Kanaya, S.; Imai, Y.; Komine, N.; Hirano, M.; Komiya, S. Organometallics 2005, 24, 1059.
40. (d) Esteruelas, M. A.; Hernández, Y. A.; López, A. M.; Oliván, M.; Oñate, E. Organometallics 2005, 24, 5989.
41. See for example:(a) Ozerov, O. V.; Watson, L. A.; Pink, M.; Caulton, K. G. J. Am. Chem. Soc. 2003, 125, 9604.
42. (b) Ozerov, O. V.; Watson, L. A.; Pink, M.; Caulton, K. G. J. Am. Chem. Soc. 2004, 126, 6363.
43. (c) Hirsekorn, K. F.; Veige, A. S.; Marshak, M. P.; Koldobskaya, Y.; Wolczanski, P. T.; Cundari, T. R.; Lobkovsky, E. B. J. Am. Chem. Soc. 2005, 127, 4809.
44. (d) Kuznetsov, V. F.; Abdur-Rashid, K.; Lough, A. J.; Gusev, D. G. J. Am. Chem. Soc. 2006, 128, 14388.