Ligand-Free Suzuki-Miyaura Cross-Coupling Reactions in Deep Eutectic Solvents: Synthesis of Benzodithiophene Derivatives and Study of their Optical and Electrochemical Performance

被引：21

作者：

Pelliccioli, Valentina ^{[1
]}

Dilauro, Giuseppe ^{[2
]}

Grecchi, Sara ^{[1
]}

Arnaboldi, Serena ^{[1
]}

Graiff, Claudia ^{[3
]}

Perna, Filippo M. ^{[2
]}

Vitale, Paola ^{[2
]}

Licandro, Emanuela ^{[1
]}

Aliprandi, Alessandro ^{[4
]}

Cauteruccio, Silvia ^{[1
]}

Capriati, Vito ^{[2
]}

机构：

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

[2] Univ Bari Aldo Moro, Consorzio CINMPIS, Dipartimento Farm Sci Farmaco, Via E Orabona 4, I-70125 Bari, Italy

[3] Univ Parma, Dipartimento Sci Chim Vita & Sostenibilita Ambien, Parco Area Sci 17-A, I-43124 Parma, Italy

[4] Univ Strasbourg, ISIS, 8 Allee Gaspard Monge, F-67083 Strasbourg, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 45期

关键词：

Benzodithiophene; Cross-coupling; Deep Eutectic Solvents; Green chemistry; Sulfur heterocycles; ORGANIC-DYES; SERIES; ROUTE;

D O I：

10.1002/ejoc.202000889

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report that dihalogeno-substituted benzodithiophenes (BDTs) undergo a smooth ligand-free Suzuki-Miyaura cross-coupling reaction, under air and moderate heating (60 degrees C), with aryl-, alkenyl- and alkynyltrifluoroborate salts in a biodegradable choline chloride-based eutectic mixture, thereby granting access to valuable pi-conjugatedBDTcompounds (up to 79 % yield), which are gaining great interest in the field of material sciences. The optical and electrochemical properties of these systems have been thoroughly investigated by means of absorption and cyclic voltammetry measurements. The first electrooligomerization study of a representativeBDTderivative has also been undertaken.

引用

页码：6981 / 6988

页数：8

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