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

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.

Diversification of the Renewable Furanic Platform via 5-(Chloromethyl)furfural-Based Carbon Nucleophiles.

Biobased 5-(chloromethyl)furoate and 5-methylfuroate esters can be deprotonated to function as furylogous lithium enolates, and the former can also undergo zinc insertion to access Reformatsky-type chemistry. Carbon nucleophilicity represents hitherto little-explored reactivity in these key carbohydrate-derived platform molecules, expanding their synthetic utility and potentially opening up new sustainable product markets (e. g.