Iridium-catalysed isomerising trialkylsilylation of methyl oleate

•An isomerising silylation reaction for methyl oleate was established.•Up to 69% of terminal vinylsilanes were obtained using an iridium-based catalyst.•Three reference compounds were synthesised and characterised.

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 CC 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.

Graphical abstractMethyl oleate undergoes [Ir(OMe)(cod)]2-catalysed dehydrogenative silylation with triethylsilane to give terminal vinylsilane products in 69% yield.Figure optionsDownload full-size imageDownload as PowerPoint slide