Abstract
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.
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