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Electrochemical Incorporation of Electrophiles into the Biomass‐Derived Platform Molecule 5‐(Chloromethyl)furfural

Von Wiley-VCH zur Verfügung gestellt

Reagent-free electrosynthesis is an emergent methodology in sustainable chemistry and is applied here to a derivative of 5-(chloromethyl)furfural (CMF), one of the most versatile biobased platform molecules. Incorporating the greenhouse gas CO2 into this platform gives a diacid derivative that is formally a furylogous malonate. Moreover, cathodic dehalogenation of CMF is also seen as superior to the use of chemical reducing agents.


Abstract

The 5-(chloromethyl)furfural (CMF) derivative ethyl 5-(chloromethyl)furan-2-carboxylate undergoes two-electron electrochemical reduction in a simple, undivided cell to give the corresponding furylogous enolate anion, which can either be quenched with carbon dioxide to give a 5-(carboxymethyl)furan-2-carboxylate or with hydrogen ion to give a 5-methylfuran-2-carboxylate, thereby expanding the derivative scope of CMF as a biobased platform molecule.

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