Metathesis of Unsaturated Fatty Acid Esters with a Reusable Ruthenium Catalyst

Significance Metathesis of unsaturated fatty acid esters with a magnetic nanoparticle-supported Hoveyda-Grubbs catalyst 1 was described. Thus, self-metathesis of methyl oleate ( 2 ) was ­carried out in the presence of the immobilized Grubbs II catalyst 1 grafted onto magnetic nanoparticles (100 nm, matrix with starch) [ 2 / 1 (mol/mol) = 2008] to give dimethyl-9-octadecene-1,18-dioate ( 3 ) in 73% yield with 489 h -¹ TOF. Cross-metathesis of methyl oleate ( 2 ) and methyl acrylate ( 5 ) with 1 [ 2 / 1 (mol/mol) = 497] gave dimethyl undec-2-en-1,11-dioate ( 6 ) in 60% yield with 12 h -¹ TOF. Self-metathesis of a macro-monomer 8 using 1 [ 8 / 1 (mol/mol) = 98] ­afforded a polymer 9 in 90% yield with 29 h -¹ TOF.