A new ruthenium-based olefin metathesis catalyst coordinated with 1,3-dimesityl-1,4,5,6-tetrahydropyrimidin-2-ylidene: Synthesis, X-ray structure, and reactivity

Organometallics

Volumn 23, Issue 18, 2004, Pages 4172-4173

  Yun, Jaesook ^a,b   Marinez, Eric R ^a   Grubbs, Robert H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b Ajou University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE MOIETY; METAL CARBENE; METATHESIS; PROXIMITY;

CATALYSIS; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; POLYMERIZATION; RUTHENIUM COMPOUNDS; SATURATION (MATERIALS COMPOSITION); SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

OLEFINS;

EID: 4444283654     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034369j     Document Type: Article

References (15)

1. Some recent reviews: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
2. Some recent reviews: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
3. Some recent reviews: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
4. Lappert has described rhodium complexes containing the ligand 1,3-dimethyl-l,4,5,6-tetrahydropyrimidin-2-ylidene: (a) Hitchcock, P. B.; Lappert, M. F.; Pye, P. L. J. Chem. Soc., Dalton Trans. 1977, 2160-2172. (b) Doyle, M. J.; Lappert, M. F.; Pye, P. L.; Terreros, P. J. Chem. Soc., Dalton Trans. 1984, 2355-2364.
5. Lappert has described rhodium complexes containing the ligand 1,3-dimethyl-l,4,5,6-tetrahydropyrimidin-2-ylidene: (a) Hitchcock, P. B.; Lappert, M. F.; Pye, P. L. J. Chem. Soc., Dalton Trans. 1977, 2160-2172. (b) Doyle, M. J.; Lappert, M. F.; Pye, P. L.; Terreros, P. J. Chem. Soc., Dalton Trans. 1984, 2355-2364.
6. Bazinet, P.; Yap, G. P. A.; Eicheson, D. S. J. Am. Chem. Soc. 2003, 125, 13314-13315.
7. (a) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
8. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
9. (c) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155.
10. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
11. (b) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416-2419.
12. 6): δ 22.53 ppm.
13. 1H NMR spectrum of the crude product consistently shows a 50-75% conversion to the desired 4. However, upon purification by column chromatography, significant decomposition occurs.
14. 2 yielded a final R1 value of 0.0305 and wR2 value of 0.0521. Crystallographic data have been deposited at the CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K., and copies can be obtained on request, free of charge, by quoting the publication citation and the deposition number 186478.
15. Bielawski, C. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 2903-2906.