Iridium-catalysed isomerising trialkylsilylation of methyl oleate

Monounsaturated fatty acids from vegetable oils are attractive substrates for applications as renewable feedstock in polymer industry. Applying the concept of transition metal-catalysed isomerising functionalisation, their nearly inaccessible internal Cdouble bond; length as m-dashC double bond can be transformed into products with a functional group in the terminal position. In this work, methyl oleate is shown to undergo [Ir(OMe)(cod)]2-catalysed dehydrogenative silylation with triethylsilane to give terminal vinylsilanes 4 in 69% yield. Independent preparation of reference substances is helpful in identifying the desired products in gas chromatograms of complex reaction mixtures.