ortho-Tolyl 2nd Generation Grubbs Catalyst

by Jean-Baptiste Bourg on February 16, 2010

ortho-Tolyl 2nd Generation Grubbs Catalyst

ortho-Tolyl 2nd Generation Grubbs Catalyst1
(Ph = phenyl)
- CAS#: [927429-60-5]
- FW: 793.28
- Color: Brown
- Initiation temperature: >20 °C

Process Strengths Weaknesses
CM -hindered alpha olefins -trisubstituted olefins
RCM -sterically hindered di- and tri-substituted olefins
-tetrasubstituted olefins
 

 
This catalyst was the product of a rational design effort to make catalysts that were efficient at forming tetrasubstituted olefins by RCM. The free ortho position on the phenyl groups in the N-heterocyclic carbene ligand leave space around the ruthenium atom for hindered substrates. While it hasn’t received as much attention as its Hoveyda version, it has shown promise in the metathesis of hindered substrates.

1 Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589.

CM – Cross Metathesis
RCM – Ring Closing Metathesis

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