Selective Conversion of Various Monosaccharaides into Sugar Acids by Additive-Free Dehydrogenation in Water

Abstract

Abundant sugars of five and six carbon atoms are promising candidates for the production of valuable platform chemicals. Here, we describe the catalytic dehydrogenation of several pentoses and hexoses into their corresponding sugar acids with the concomitant formation of molecular hydrogen. This biomass transformation is promoted by highly active and selective catalysts based on iridium(III) complexes containing a triazolylidene (trz) as ligand. Monosaccharides are converted into sugar acids in an easy and sustainable manner using only catalyst and water, and in contrast to previously reported procedures, in the absence of any additive. The reaction is therefore very clean, and highly selective, which avoids the tedious purification and product separation. Mechanistic investigations using 1H NMR and UV-vis spectroscopies and ESI mass spectrometry (ESI-MS) indicate the formation of an unprecedented diiridium-hydride as dormant species that correspond to the catalyst resting state.