Pyrroles are important building blocks in many areas of chemistry, pharmaceuticals and materials. Pyrroles are currently fossil-based and transition to renewable alternatives demands new synthetic pathways. The use of biomass is a very attractive option for more sustainable solutions and several bulk and fine chemical are already produced from biomass. 2,5-Dimethoxytetrahydrofuran is an example of fine chemical derived from carbohydrate fraction of biomass. Here we report the synthesis of N-substituted pyrroles through a modified Clauson-Kass protocol starting from 2,5-dimethoxytetrahydrofuran. The proposed method allows to obtain pyrroles under mild reaction conditions and it can be performed catalyst-free. The protocol works both in continuous flow and under batch conditions.. A wide range of anilines and sulphonamides are transformed to corresponding N-substituted pyrroles in good to excellent yields. Conductive films are achieved through electropolymerization and they show distinct redox activity. Current efforts entail the application of the material in sensors or energy storage devices. The proposed method opens the pathway to sustainable biomass-based organic electronics.

Toward biomass-based organic electronics: Continuous flow synthesis and electropolymerization of N-substituted polypyrroles

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