Augmentation of productivity in olefin cross-metathesis: maleic acid does the trick!

Abstract

Herein, the effect of subtle substrate modifications on the cross-metathesis (CM) catalyzed by ruthenium complexes is presented. The presence of a carboxylic acid moiety in the substrate (i.e. maleic acid – MA-H) was shown to positively influence the outcome of the reaction even for complexes that normally do not perform well with analogous esters (maleates or acrylates). In the cross-metathesis reaction of methyl oleate (MO) with MA-H, good conversion (92%) and good selectivity towards the CM products (92%) were achieved with low catalyst loadings. Additionally, the scope of the reaction was expanded to a variety of vegetable oils.