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Issue 15, 2017
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Selective palladium-catalysed synthesis of diesters: alkoxycarbonylation of a CO2-butadiene derived δ-lactone

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Abstract

Novel unsaturated C10 diesters are produced via the alkoxycarbonylation of δ-lactone 1 (3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one), derived from the telomerization of CO2 and butadiene. The key for the selective valorization of 1 is the use of a catalytic system based on PdCl2, a chelating phosphine bearing electron-withdrawing groups and an acidic promoter. The unsaturated C10 methyl diester can be easily hydrogenated on Pd/C under mild conditions to afford its corresponding saturated diester. Subsequent hydrogenation using the homogeneous [Ru(acac)3]/Triphos catalysts gives 2-ethyloctane-1,8-diol in high yield. The overall procedure allows synthesizing new building blocks for the manufacturing of renewable polymers and polymer processing materials.

Graphical abstract: Selective palladium-catalysed synthesis of diesters: alkoxycarbonylation of a CO2-butadiene derived δ-lactone

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Publication details

The article was received on 08 May 2017, accepted on 09 Jun 2017 and first published on 26 Jun 2017


Article type: Paper
DOI: 10.1039/C7GC01366C
Citation: Green Chem., 2017,19, 3542-3548
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    Selective palladium-catalysed synthesis of diesters: alkoxycarbonylation of a CO2-butadiene derived δ-lactone

    F. Ferretti, M. Sharif, S. Dastgir, F. Ragaini, R. Jackstell and M. Beller, Green Chem., 2017, 19, 3542
    DOI: 10.1039/C7GC01366C

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