β-H transfer from the metallacyclobutane: A key step in the deactivation and byproduct formation for the well-defined silica-supported rhenium alkylidene alkene metathesis catalyst

Journal of the American Chemical Society

Volumn 130, Issue 19, 2008, Pages 6288-6297

  Leduc, Anne Marie ^a   Salameh, Alain ^a   Soulivong, Daravong ^a   Chabanas, Mathieu ^a   Basset, Jean Marie ^a   Copéret, Christophe ^a   Solans Monfort, Xavier ^b,c   Clot, Eric ^b   Eisenstein, Odile ^b   Böhm, Volker P W ^d   Röper, Michael ^d  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^d BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BYPRODUCTS; CATALYST ACTIVITY; ENERGY BARRIERS; SILICA;

BYPRODUCT FORMATION; METALLACYCLOBUTANE; RHENIUM ALKYLIDENE ALKENE METATHESIS;

RHENIUM COMPOUNDS;

ALKENE; ALKENE DERIVATIVE; CYCLOBUTANE DERIVATIVE; ETHYLENE; LIGAND; PROPYLENE; RHENIUM; SILICON DIOXIDE;

ARTICLE; CATALYST; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ENERGY; HYDROGEN BOND; MOLECULAR MODEL;

EID: 43249115667     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800189a     Document Type: Article

References (44)

1. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18–29.
2. Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592–4633.
3. Mol, J. C. Top. Catal. 2004, 27, 97–104.
4. Mol, J. C. J. Mol. Catal. A 2004, 213, 39–45.
5. Ivin, K. J.; Mol, I. C. Olefin Metathesis and Metathesis Polymerization, 2nd ed.; Academic Press: San Diego, 1996.
6. Chen, X.; Zhang, X.; Chen, P. Angew. Chem., Int. Ed. 2003, 42, 3798–3801.
7. Zhang, X.; Chen, X.; Chen, P. Organometallics 2004, 23, 3437–3447.
8. Narancic, S.; Chen, P. Organometallics 2005, 24, 10–12.
9. Salameh, A.; Copéret, C.; Basset, J.-M.; Bohm, V. P. W.; Roper, M. AdV. Synth. Catal. 2007, 349, 238–242.
10. Chabanas, M.; Baudouin, A.; Copéret, C.; Basset, J.-M. J. Am. Chem. Soc. 2001, 123, 2062–2063.
11. Chabanas, M.; Baudouin, A.; Copéret, C.; Basset, J.-M.; Lukens, W.; Lesage, A.; Hediger, S.; Emsley, L. J. Am. Chem. Soc. 2003, 125, 492–504.
12. Copéret, C. New J. Chem. 2004, 28, 1–10.
13. Solans-Monfort, X.; Clot, E.; Copéret, C.; Eisenstein, O. Organometallics 2005, 24, 1586–1597.
14. Chabanas, M.; Copéret, C.; Basset, J.-M. Chem.—Eur. J. 2003, 9, 971–975.
15. Bilhou, J. L.; Basset, J. M.; Mutin, R.; Graydon, W. F. J. Am. Chem. Soc. 1977, 99, 4083–4090.
16. Kapteijn, F.; Bredt, H. L. G.; Homburg, E.; Mol, J. C. Ind. Eng. Chem., Prod. Res. DeV. 1981, 20, 457–466.
17. Chauvin, Y.; Commereuc, D. J. Chem. Soc., Chem. Commun. 1992, 462–464.
18. All alkenes could be observed and identified by GC and GC/MS, but the couples (E)-2-butene/1-butene and 1-pentene/2-methyl-1-butene could only be partially separated, which led to somewhat imprecise relative quantification of these products.
19. Salameh, A.; Baudouin, A.; Soulivong, D.; Boehm, V.; Roeper, M.; Basset, J.-M.; Copéret, C. J. Catal. 2008, 253, 180–190.
20. Burdett, K. A.; Harris, L. D.; Margl, P.; Maughon, B. R.; Mokhtar-Zadeh, T.; Saucier, P. C.; Wasserman, E. P. Organometallics 2004, 23, 2027–2047.
21. Herisson, J. L.; Chauvin, Y. Makromol. Chem. 1971, 141, 161–176.
22. Fox, H. H.; Schofield, M. H.; Schrock, R. R. Organometallics 1994, 13, 2804–2815.
23. Cundari, T. R.; Gordon, M. S. Organometallics 1992, 11, 55–63.
24. Folga, E.; Ziegler, T. Organometallics 1993, 12, 325–337.
25. Monteyne, K.; Ziegler, T. Organometallics 1998, 17, 5901–5907.
26. Wu, Y.-D.; Peng, Z.-H. J. Am. Chem. Soc. 1997, 119, 8043–8049.
27. Wu, Y.-D.; Peng, Z.-H. Inorg. Chem. Acta 2003, 345, 241–254.
28. Solans-Monfort, X.; Clot, E.; Copéret, C.; Eisenstein, O. J. Am. Chem. Soc. 2005, 127, 14015–14025.
29. Poater, A.; Solans-Monfort, X.; Clot, E.; Copéret, C.; Eisenstein, O. Dalton Trans. 2006, 3077–3087.
30. Rhers, B.; Quadrelli, E. A.; Baudouin, A.; Taoufik, M.; Copéret, C.; Lefebvre, F.; Basset, J.-M.; Fenet, B.; Sinha, A.; Schrock, R. R. J. Organomet. Chem. 2006, 691, 5448–5455.
31. Solans-Monfort, X.; Filhol, J.-S.; Copéret, C.; Eisenstein, O. New J. Chem. 2006, 30, 842–850.
32. Poater, A.; Solans-Monfort, X.; Clot, E.; Copéret, C.; Eisenstein, O. J. Am. Chem. Soc. 2007, 129, 8207–8216.
33. Goumans, T. P. M.; Ehlers, A. W.; Lammertsma, K. Organometallics 2005, 24, 3200–3206.
34. Szabo, M. J.; Berke, H.; Weiss, T.; Ziegler, T. Organometallics 2003, 22, 3671–3677.
35. Tobisch, S. Organometallics 2007, 26, 6529–6532.
36. Tsang, W. C. P.; Hultzsch, K. C.; Alexander, J. B.; Bonitatebus, P. J., Jr.; Schrock, R. R.; Hoveyda, A. H J. Am. Chem. Soc. 2003, 125, 2652–2666.
37. Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748–3759.
38. Lopez, L. P. H.; Schrock, R. R. J. Am. Chem. Soc. 2004, 126, 9526–9527.
39. Perdew, J. P.; Wang, Y. Phys. ReV. B 1992, 45, 13244–13249.
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648–5652.
41. Frisch, M. J. et al. Gaussian03; Gaussian Inc.: Pittsburgh, PA, 2003.
42. Andrae, D.; Haeussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123–141.
43. Bergner, A.; Dolg, M.; Kuechle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431–1441.
44. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213–222.