A biomass-derived safe medium to replace toxic dipolar solvents and access cleaner Heck coupling reactions

被引：113

作者：

Strappaveccia, Giacomo ^{[1
]}

Ismalaj, Ermal ^{[1
]}

Petrucci, Chiara ^{[1
]}

Lanari, Daniela ^{[2
]}

Marrocchi, Assunta ^{[1
]}

Drees, Martin ^{[3
]}

Facchetti, Antonio ^{[4
,5
,6
]}

Vaccaro, Luigi ^{[1
]}

机构：

[1] Univ Perugia, CEMIN Dipartimento Chim Biol & Biotecnol, Lab Green Synthet Organ Chem, I-06123 Perugia, Italy

[2] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, I-06123 Perugia, Italy

[3] Polyera Corp, Skokie, IL 60077 USA

[4] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

[5] Northwestern Univ, Mat Res Ctr, Evanston, IL 60208 USA

[6] King Abdulaziz Univ, Ctr Excellence Adv Mat Res, Jeddah 21413, Saudi Arabia

来源：

GREEN CHEMISTRY | 2015年 / 17卷 / 01期

关键词：

GAMMA-VALEROLACTONE; GREEN CHEMISTRY; CATALYTIC CONVERSION; PALLADIUM CATALYSTS; LEVULINIC ACID; ALPHA; BETA-UNSATURATED KETONES; MEDICINAL CHEMISTRY; CONJUGATED POLYMERS; REUSABLE CATALYST; REACTION MIXTURES;

D O I：

10.1039/c4gc01677g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

gamma-Valerolactone (GVL) is an excellent reaction medium, derived from biomasses, which can replace classic dipolar aprotic media such as DMF or NMP. In this contribution, we have investigated the use of GVL in the palladium-catalyzed Heck reaction and accessed the clean synthesis of several small molecules. Furthermore, we optimized a GVL-based protocol to synthesize a poly(phenylenevinylene) (PPV) derivative in high yields and purity, and with very low Pd-content. Finally, we demonstrated that GVL is superior to conventional dipolar media in terms of controlling palladium impurities, which may influence the performance of certain optoelectronic devices such as organic solar cells and field-effect transistors.

引用

页码：365 / 372

页数：8

共 102 条

[61] Direct arylation polycondensation: A promising method for the synthesis of highly pure, high-molecular-weight conjugated polymers needed for improving the performance of organic photovoltaics [J].