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 C = C 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(O-Me)(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. (C) 2013 Elsevier B.V. All rights reserved.