A thermally switchable latent ruthenium olefin metathesis catalyst

Organometallics

Volumn 27, Issue 5, 2008, Pages 811-813

  Ben Asuly, Amos ^b   Tzur, Eyal ^a   Diesendruck, Charles E ^a   Sigalov, Mark ^a   Goldberg, Israel ^c   Lemcoff, N Gabriel ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b ACHVA ACADEMIC COLLEGE   (Israel)

^c TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHELATION; OLEFINS; RUTHENIUM COMPOUNDS; THERMODYNAMIC STABILITY;

DIETHYL DIALLYLMALONATE; METATHESIS CATALYSTS; ROOM TEMPERATURE; RUTHENIUM OLEFINS;

ORGANOMETALLICS;

EID: 42149097199     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om701180z     Document Type: Article

References (24)

1. Grubbs, R. H. Chem. Sci. 2007, Aug 20.
2. (a) Louie, J.; Grubbs, R. H. Organometallics 2002, 21, 2153-2164.
3. (b) Zhang, Y.; Wang, D.; Lönnecke, P.; Scherzer, T.; Buchmeiser, M. R. Macromol. Symp. 2006, 236, 30-37.
4. (c) Delaude, L.; Delfosse, S.; Richel, A.; Demoneeau, A.; Noels, A. F. Chem. Commun. 2003, 1526-1527.
5. (d) van der Schaaf, P. A.; Kolly, R.; Kirner, H.; Rime, F.; Mühlebach, A.; Hafner, A. J. Organomet. Chem. 2000, 606, 65-74.
6. (a) Gstrein, X.; Burtscher, D.; Szadkowska, A.; Brabasiewicz, M.; Stelzer, F.; Grela, K.; Slugovc, C. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 3494-3500.
7. (b) Slugovc, C.; Perner, B.; Stelzer, F.; Mereiter, K. Organometallics 2004, 23, 3622-3626.
8. (c) Denk, K.; Fridgen, J.; Herrmann, W. A. Adv. Synth. Catal. 2002, 344, 666-670.
9. (d) See also ref 2d.
10. (e) Barbasiewicz, M.; Szadkowska, A.; Bujok, R.; Grela, K. Organometallics 2006, 25, 3599-3604.
11. (f) Hejl, A.; Day, M. W.; Grubbs, R. H. Organometallics 2006, 25, 6149-6154.
12. (g) Chang, S.; Jones, L., II; Wang, C.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 3460-3465.
13. (a) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976.
14. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
15. (a) Gawin, R.; Makal, A.; Wozniak, K.; Mauduit, M.; Grela, K. Angew. Chem., Int. Ed. 2007, 46, 7206-7209.
16. (b) See also; P'Pool, S. J.; Schanz, H.-J. J. Am. Chem. Soc. 2007, 129, 14200-14212.
17. Zhang, H. Q.; Xia, Z.; Kolasa, T.; Dinges, J. Tetrahedron Lett. 2003, 44, 8661-8663.
18. 1H NMR suggests that one of the byproducts is the trans-dichloro derivative, while the other byproduct is a six-coordinated compound which still contains the tricyclohexylphosphine ligand. These two byproducts were shown to convert to 5 upon standing at room temperature, making their full characterization more complicated but raising the yield of 5 from 55% to 64% (see the Supporting Information).
19. For examples of other metal-NHC rotation barriers, see: (a) Dible, B. R.; Sigman, M. S. Inorg. Chem. 2006, 45, 8430-8431.
20. (b) Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663-1667.
21. 3, R1 = 0.066 for 6395 reflections with I > 2σ(I).
22. Kim, M.; Eum, M.; Jin, M. Y.; Jun, K.; Lee, C. W.; Kuen, K. A.; Kim, C. H.; Chin, C. S. J. Organomet. Chem. 2004, 689, 3535-3540.
23. Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 5740-5745.
24. Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 6786-6801.