Valorization of 2,5-furandicarboxylic acid. Diels-Alder reactions with benzyneElectronic supplementary information (ESI) available. See DOI: 10.1039/c8gc00308d

Biomass-derived 2,5-furandicarboxylic acid was valorized by conversion to 1,4-naphthalenedicarboxylic acid via benzyne-cycloaddition and reductive aromatization in 66% overall yield (four steps). Two novel bicyclic intermediates were isolated in 80% and 98% yield. These advances diversify the potential end uses of renewable terephalic acid analogs and other furanics available from cellulose biorefinery. Biomass-derived 2,5-furandicarboxylic acid was valorized by conversion to 1,4-naphthalenedicarboxylic acid via benzyne-cycloaddition and reductive aromatization in 66% overall yield (four steps).