We report that dihalogeno-substituted benzodithiophenes (BDTs) undergo a smooth ligand-free Suzuki–Miyaura cross-coupling reaction, under air and moderate heating (60 °C), with aryl-, alkenyl- and alkynyltrifluoroborate salts in a biodegradable choline chloride-based eutectic mixture, thereby granting access to valuable π-conjugated BDT compounds (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 representative BDT derivative has also been undertaken.

Ligand-Free Suzuki–Miyaura Cross-Coupling Reactions in Deep Eutectic Solvents : Synthesis of Benzodithiophene Derivatives and Study of their Optical and Electrochemical Performance / V. Pelliccioli, G. Dilauro, S. Grecchi, S. Arnaboldi, C. Graiff, F.M. Perna, P. Vitale, E. Licandro, A. Aliprandi, S. Cauteruccio, V. Capriati. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (2020). [Epub ahead of print] [10.1002/ejoc.202000889]

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

V. Pelliccioli
Primo
;
S. Grecchi;S. Arnaboldi;P. Vitale;E. Licandro;S. Cauteruccio
Penultimo
;
2020

Abstract

We report that dihalogeno-substituted benzodithiophenes (BDTs) undergo a smooth ligand-free Suzuki–Miyaura cross-coupling reaction, under air and moderate heating (60 °C), with aryl-, alkenyl- and alkynyltrifluoroborate salts in a biodegradable choline chloride-based eutectic mixture, thereby granting access to valuable π-conjugated BDT compounds (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 representative BDT derivative has also been undertaken.
Benzodithiophene; Cross-coupling; Deep Eutectic Solvents; Green chemistry; Sulfur heterocycles
Settore CHIM/06 - Chimica Organica
   PIANO DI SOSTEGNO ALLA RICERCA 2015-2017 - LINEA 2 "DOTAZIONE ANNUALE PER ATTIVITA' ISTITUZIONALE" (2015)
2020
ago-2020
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/767079
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