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French scientists report a ruthenium-catalysed cross-metathesis route to produce a C12 nitrile ester with high turnover number.

10-Undecylenic acid derivatives are a valuable feedstock readily available from caster oil and have been used for the industrial production of polyamide.  In this work, scientists from CBRS-University of Rennes and ARKEMA in France demonstrate that the linear C12 α,ω-amino ester, a precursor to polyamide, can be prepared viacross-metathesis of methyl acrylate with 10-undecenenitrile (which is bio-sourced) in the presence of ruthenium-alkylidene catalysts.  Subsequent C=C and nitrile reduction could then be performed to produce the C12 α,ω-amino ester.

This overall tandem procedure provides a sustainable route to linear amino esters, where a single catalyst is used from the outset to perform 3 catalytic transformations (cross-metathesis, carbon-carbon double bond hydrogenation and nitrile reduction) using bio-sourced starting materials.

This article is free to access until the 6th August 2012! Click on the link below to find out more…

Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis, X. Miao, C. Fischmeister, P. H. Dixneuf, C. Bruneau, J.-L. Dubois and J.-L. Couturier, Green Chem., 2012, DOI: 10.1039/C2GC35648A

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