Novel ruthenium(II)2 carboxylates as catalysts for alkene metathesis

Chemistry - A European Journal

Volumn 7, Issue 13, 2001, Pages 2842-2847

  Buchowicz, Wlodzimierz ^a   Ingold, Florent ^a   Mol, Johannes C ^a   Lutz, Martin ^b   Spek, Anthony L ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Alkenes; Homogenous catalysis; Metathesis; Ruthenium carbenes

Indexed keywords

CARBOXYLATION; COMPLEXATION; ESTERS; FATTY ACIDS;

METATHESIS;

CATALYSTS;

ALKENE; CARBENE; CARBOXYLIC ACID; RUTHENIUM; SATURATED FATTY ACID; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; POLYMERIZATION; SYNTHESIS;

EID: 0035796445     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010702)7:13<2842::AID-CHEM2842>3.0.CO;2-O     Document Type: Article

References (44)

1. K. J. Ivin, J. C. Mol, Olefin Metathesis and Metathesis Polymerization, Academic Press, San Diego, 1997.
2. R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robbins, M. DiMare, M. O'Regan, J. Am. Chem. Soc. 1990, 112, 3875.
3. G. C. Bazan, E. Khosravi, R. R. Schrock, W. J. Feast, V. C. Gibson, M. B. O'Regan, J. K. Thomas, W. M. Davis, J. Am. Chem. Soc. 1990, 112, 8378.
4. G. C. Bazan, J. H. Oskam, H-N. Cho, L. Y. Park, R. R. Schrock, J. Am. Chem. Soc. 1991, 113, 6899.
5. S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1993, 115, 9858.
6. P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem. 1995, 107, 2179;
7. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
8. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100.
9. M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124;
10. Angew. Chem. Int. Ed. Engl. 1997, 36, 2037.
11. R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413.
12. Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998.
13. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. 1998, 110, 2631;
14. Angew. Chem. Int. Ed. 1998, 37, 2490.
15. M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247.
16. J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674.
17. L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787.
18. T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573;
19. Angew. Chem. Int. Ed. 1999, 38, 2416.
20. M. Scholl, S. Ding, C. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953.
21. J. Huang, H-J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5375.
22. a) L. Jafarpour, E. D. Stevens, S. P. Nolan, J. Organomet. Chem. 2000, 606, 49;
23. b) L. Jafarpour, S. P. Nolan, Organometallics 2000, 19, 2055.
24. Z. Wu, S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1995, 117, 5503.
25. E. L. Dias, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1997, 119, 3887.
26. S. Chang, L. Jones II, C. Wang, L. M. Henling, R. H. Grubbs, Organometallics 1998, 17, 3460.
27. S. M. Hansen, M. A. O. Volland, F. Rominger, F. Eisenträger, P. Hofmann, Angew. Chem. 1999, 111, 1360;
28. Angew. Chem. Int. Ed. 1999, 38, 1273.
29. W. Buchowicz, J. C. Mol, M. Lutz, A. L. Spek, J. Organomet. Chem. 1999, 588, 205.
30. This interpretation is in contrast to the findings of Chen and co-workers (C. Adlhart, C. Hinderling, H. Baumann, P. Chen, J. Am. Chem. Soc. 2000, 122, 8204), who observed that in the gas phase increasing electron deficiency at the Ru centre enhances the activity. However, in their work only the metathesis step was investigated, that is a reaction of a Ru carbene with 1-butene after dissociation of one phosphine ligand. We interpret our data in terms of the carboxylates affecting the initial ligand dissociation.
31. See also C. Adlhart, M. A. O. Volland, P. Hofmann, P. Chen, Helv. Chim. Acta 2000, 83, 3306.
32. J. A. Tallarico, P. J. Bonitatebus, M. L. Snapper, J. Am. Chem. Soc. 1997, 119, 7157.
33. J. J. Eisch, G. R. Husk, J. Org. Chem. 1966, 31, 589.
34. P. Sartori, M. Weidenbruch, Chem. Ber. 1967, 100, 3016.
35. G. Wulff, G. Röhle, W. Krüger, Chem. Ber. 1972, 105, 1097.
36. Complexes 3-7 crystallise with variable amounts of solvent (hexane). Therefore correct elemental analyses could not obtained in some cases.
37. J. E. McMurry, M. P. Fleming, K. L. Kees, L. R. Krepski, J. Org. Chem. 1978, 43, 3255.
38. A. J. M. Duisenberg, J. Appl. Crystallogr. 1992, 25, 92.
39. A. J. M. Duisenberg, Ph.D. thesis, Utrecht University (The Netherlands), 1998.
40. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, The DIRDIF97 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1997.
41. R. Herbst-Irmer, G. M. Sheldrick, Acta Crystallogr. Sect. B 1998, 54, 443.
42. G. M. Sheldrick, SHELXL97. Program for crystal structure refinement, University of Göttingen, Germany, 1997.
43. A. L. Spek, PLATON. A multipurpose crystallographic tool, Utrecht University, The Netherlands, 2000.
44. W. Buchowicz, J. C. Mol, J. Mol. Catal. 1999, 148, 97.