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.

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