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Long-chain α–ω diols from renewable fatty acids via tandem olefin metathesis–ester hydrogenation

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Abstract

Long chain α–ω diols were readily accessed from renewable fatty acid methyl esters following an orthogonal tandem self-metathesis–ester hydrogenation protocol. By adding a base and a bidentate ligand, the metathesis catalysts were transformed in situ into efficient ester hydrogenation catalysts. The selectivity of the hydrogenation reaction was tuned towards the exclusive formation of either the unsaturated or the saturated diol by modifying the ligand/catalyst ratio. An orthogonal tandem cross-metathesis–ester hydrogenation reaction was also applied for the synthesis of a fragrance compound.

Graphical abstract: Long-chain α–ω diols from renewable fatty acids via tandem olefin metathesis–ester hydrogenation

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Publication details

The article was received on 16 Jan 2017, accepted on 08 Mar 2017, published on 09 Mar 2017 and first published online on 09 Mar 2017


Article type: Communication
DOI: 10.1039/C7GC00192D
Citation: Green Chem., 2017, Advance Article
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    Long-chain α–ω diols from renewable fatty acids via tandem olefin metathesis–ester hydrogenation

    A. Gonzalez-de-Castro, E. Cosimi, M. J. B. Aguila, P. Gajewski, M. Schmitkamp, J. G. de Vries and L. Lefort, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC00192D

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