2ndGeneration Hoveyda Catalyst1
– CAS#: [301224-40-8]
– FW: 626.62
– Color: Green
– Initiation temperature: >0 °C
|CM2||-Compatible with most olefins, including highly electron-deficient (i.e. acrylonitrile)||-Incompatible with hindered substrates|
|RCM||-Forms di- and trisubstituted olefins rapidly (5- & 6-membered rings)
-Excels at macrocycle formation
|-Tetrasubstituted olefin formation is slow and requires high catalyst loadings
-Incompatible with hindered substrates
Independently synthesized in 2000 by the Hoveyda and Blechert groups, this catalyst has become commonly known as the 2nd Generation Hoveyda (or Hoveyda-Grubbs) Catalyst. It’s considered one of the best catalysts around for cross metathesis (CM) and ring closing metathesis (RCM) because it works in most circumstances and is usually more reactive than the 2nd Generation Grubbs Catalyst at lower temperatures. It’s useful for the efficient metathesis of electron-deficient substrates. This catalyst hasn’t found much use in ring opening metathesis polymerization (ROMP) applications due in part to its cost. It is best made starting from another metathesis catalyst, so it remains a high-price, high performance option.
1 (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc., 2000, 122, 8168; (b) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett., 2000, 41, 9973-9976.
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