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

被引：15

作者：

Ferretti, Francesco ^{[1
,2
]}

Sharif, Muhammad ^{[1
,3
]}

Dastgir, Sarim ^{[4
,5
]}

Ragaini, Fabio ^{[2
]}

Jackstell, Ralf ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany

[2] Univ Milan, Dipartimento Chim, Via C Golgi 19, I-20133 Milan, Italy

[3] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia

[4] Hamad Bin Khalifa Univ, Qatar Environm & Energy Res Inst, Qatar Fdn, Doha 34110, Qatar

[5] Hamad Bin Khalifa Univ, Coll Sci & Engn, Doha, Qatar

来源：

GREEN CHEMISTRY | 2017年 / 19卷 / 15期

关键词：

CARBON-DIOXIDE; HYDROGENATION; BUTADIENE; ALCOHOLS; ESTERS; TELOMERIZATION; ACTIVATION; REDUCTION; COMPLEXES; EFFICIENT;

D O I：

10.1039/c7gc01366c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel unsaturated C-10 diesters are produced via the alkoxycarbonylation of delta-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 C-10 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.

引用

页码：3542 / 3548

页数：7

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