Abstract
Direct (hetero)arylation (DHA) is playing a key role in improving the efficiency and atom economy of C–C cross coupling reactions, so has impacts in pharmaceutical and materials chemistry. Current research focuses on further improving the generality, efficiency and selectivity of the method through careful tuning of the reaction conditions and the catalytic system. Comparatively fewer studies are dedicated to the replacement of the high-boiling-point organic solvents dominating the field and affecting the overall sustainability of the method. We show herein that the use of a 9:1 v/v emulsion of an aqueous Kolliphor 2 wt% solution while having toluene as the reaction medium enables the preparation of relevant examples of thiophene-containing π-conjugated building blocks in high yield and purity.
Highlights
Solution-processable π-conjugated organic materials are key components of a vast array of applications ranging from photonics toelectronics [1,2,3,4,5,6]
The aim of this work is the replacement with water of the organic solvent in Direct (hetero)arylation (DHA) reactions
Since high temperatures are normally required to activatearomatic C–H bonds (T ≥ 100 ◦ C), the use of a micellar solution becomes impossible, so we had to revert to oil-in-water emulsions with a minimum amount of an organic solvent
Summary
Solution-processable π-conjugated organic materials are key components of a vast array of applications ranging from photonics to (opto)electronics [1,2,3,4,5,6]. Aside from improved stability and processability, one of the main issues still hampering full industrial exploitation is the overall sustainability of the synthetic protocols [7,8,9]. Researchers working in the field of printed (opto)electronics are becoming increasingly aware of the need for materials combining reasonable performances with sustainable synthetic access [10,11]. Such an endeavor requires a certain redirection in the design criteria guiding the development of new materials and a drastic improvement of the synthetic methodologies employed [12,13]
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