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
收藏
页码：3542 / 3548
页数：7
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