1st Generation Grubbs Catalyst1
(Ph = phenyl; PCy3 = tricyclohexylphosphine)
– CAS#: [172222-30-9]
– FW: 822.95
– Color: Purple
– Initiation temperature: >20 °C
| Process | Strengths | Weaknesses |
| CM2 | -Synthesis of 1,2-disubstituted olefins from terminal olefins -Ethenolysis of internal olefins to make terminal olefins -ADMET of unhindered terminal olefins |
-Formation of trisubstituted olefins -Electron-deficient substrates -Hindered substrates |
| RCM | -Synthesis of 1,2-disubstituted olefins -Typically forms the kinetic E/Z ratio |
-Trisubstituted olefin-formation -Hindered substrates |
| ROMP | -Strained olefins | -High catalyst loadings generally required |
Although not the first to be developed, this is the compound that is generally known as the 1st Generation Grubbs Catalyst. It’s a precursor catalyst to many of the other ruthenium metathesis catalysts, so it’s one of the cheapest. It’s great if you’re trying an easy metathesis reaction (i.e. forming unhindered, unstrained products) for the first time because it tends to participate in fewer side reactions than the more active catalysts. Its long shelf-life and relatively low cost make it a common sight on the bench of organic chemists.
1 Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
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
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