Selective palladium-catalysed synthesis of diesters: Alkoxycarbonylation of a CO2-butadiene derived δ-lactone

Francesco Ferretti, Muhammad Sharif, Sarim Dastgir, Fabio Ragaini, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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.

Original languageEnglish
Pages (from-to)3542-3548
Number of pages7
JournalGreen Chemistry
Volume19
Issue number15
DOIs
StatePublished - 2017
Externally publishedYes

Fingerprint

Dive into the research topics of 'Selective palladium-catalysed synthesis of diesters: Alkoxycarbonylation of a CO2-butadiene derived δ-lactone'. Together they form a unique fingerprint.

Cite this