Selective palladium-catalysed synthesis of diesters: alkoxycarbonylation of a CO2-butadiene derived δ-lactone. Issue 15 (26th June 2017)

• Record Type: Journal Article
• Authors: Ferretti, Francesco; Sharif, Muhammad; Dastgir, Sarim; Ragaini, Fabio; Jackstell, Ralf; Beller, Matthias
• Is Part Of: Green chemistry. Volume 19:Issue 15(2017)
• Page Start: 3542
• Page End: 3548
• Publication Date: 2017-06-26
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c7gc01366c
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : A selective domino reaction has been developed for the valorization of a well-known δ-lactone synthesized by the telomerization of 1, 3-butadiene and CO2 . Abstract : Novel unsaturated C10 diesters are produced via the alkoxycarbonylation of δ-lactone1 (3-ethylidene-6-vinyltetrahydro-2 H -pyran-2-one), derived from the telomerization of CO2 and butadiene. The key for the selective valorization of1 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.