5-(Chloromethyl)furfural (CMF) is a cellulose derivative of increasing appeal as a renewable platform molecule. Although its role as an electrophile has been broadly studied, little is known about its potential utility as a carbon nucleophile. This work describes the preparation of organozinc reagents based on CMF by the insertion of zinc metal into the C−Cl bond. Reformatsky-type reactions are observed with a range of electrophiles under mild conditions in good to high yields. A kinetic study of zinc insertion shows the generation of this organometallic reagent from renewable furoate esters is a facile process. This method constitutes a practical tool in the synthetic repertory for the conversion of cellulosic biomass into useful organic molecules.

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.

Highly branched alkanes and cycloalkanes are produced via electrochemical processing of the renewable platform molecule mesityl oxide, which is a dimer of biogenic acetone. The final product is a sustainable, drop-in jet fuel.

The chemistry of furylogous malonic and cyanoacetic esters prepared from 5-(chloromethyl)furfural (CMF), a highly versatile biobased platform molecule, was investigated. Hydrogen isotope exchange data and computational results show a significant degree of remote methylene activation by the furylogy effect. The installation of strong chromophores using Knoevenagel chemistry with natural aldehydes leads to a series of biobased synthetic colorants in good to excellent yields. Fabric dyeing tests showed their potential to serve as alternatives to petrochemical dyes in the textile industry.