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Ligand‐Free Suzuki–Miyaura Cross‐Coupling Reactions in Deep Eutectic Solvents: Synthesis of Benzodithiophene Derivatives and Study of their Optical and Electrochemical Performance
Author(s) -
Pelliccioli Valentina,
Dilauro Giuseppe,
Grecchi Sara,
Arnaboldi Serena,
Graiff Claudia,
Perna Filippo M.,
Vitale Paola,
Licandro Emanuela,
Aliprandi Alessandro,
Cauteruccio Silvia,
Capriati Vito
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000889
Subject(s) - chemistry , choline chloride , eutectic system , ligand (biochemistry) , cyclic voltammetry , electrochemistry , combinatorial chemistry , aryl , derivative (finance) , conjugated system , yield (engineering) , coupling reaction , photochemistry , polymer chemistry , organic chemistry , catalysis , alkyl , polymer , materials science , electrode , biochemistry , receptor , alloy , financial economics , economics , metallurgy
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.