Advanced fine-tuning of Grubbs/Hoveyda olefin metathesis catalysts: a further step toward an optimum balance between antinomic properties

A 95% yield in the cross metathesis of acrylonitrile with a model olefin is achieved at 25 °C with only 3 mol % of the new air-stable ruthenium catalyst 1f shown in the enclosed structural diagram. Even more remarkable are the performances of its boosted version 1g incorporating an electron-withdrawing group. Both these new enhanced versions of Hoveyda catalyst are readily available from Grubbs second generation precatalyst upon reaction with a styrenyl ether the end group of which has been functionalized by an ester function. The latter acts as a weakly coordinating ligand allowing to reach a desirable balance between antinomic properties such as the catalyst's stability, a high activity for challenging substrates, and a high initiation rate. Copyright © 2006 American Chemical Society.