2nd Generation Grubbs Catalyst1
(Ph = phenyl; PCy3 = tricyclohexylphosphine)
– CAS#: [246047-72-3]
– FW: 848.97
– Color: Orange-brown
– Initiation temperature: >10 °C.
|CM2||-Applies to most olefins
-Deactivated olefins (e.g. vinyl phosphonates, α, β-unsaturated carbonyls)
-Typically forms the thermodynamic E/Z ratio
|-Highly electron-deficient substrates
-Very Hindered substrates
|RCM||-Synthesis of disubstituted and tri-substituted olefins||-Tetra-substituted olefin-formation requires high loadings
|ROMP||-Low catalyst loadings||-Propagation is faster than initiation, which can give broad polydispersities|
This catalyst is commonly known as the 2nd Generation Grubbs Catalyst, and along with the 1st Generation Grubbs Catalyst is one of the most widely-used homogenous metathesis catalysts. It provides a distinct increase in activity in all olefin metathesis reactions while maintaining functional group tolerance similar to the 1st generation system. As a consequence, it generally requires lower catalyst loadings than the 1st generation catalyst. Also, it has been used in challenging CM (e.g. 1,1-disubstituted olefins, tri-substituted olefins) or with deactivated olefins (e.g. vinyl phosphonates, α, β-unsaturated carbonyls).
1 Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett., 1999, 1, 953.
2 Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc., 2003, 125, 11360-11370.
CM – Cross Metathesis
RCM – Ring Closing Metathesis
ROMP – Ring Opening Metathesis Polymerization