Sugar Deoxygenation

Published in ACS Catalysis, the Gagné Group reports an approach to enhancing the number of valuable compounds one can synthesize in a single step from biorenewable carbon sources, cellulosics.

The group members found that diverging partial deoxygenation selectivities are made possible from cellulosic biomass derived sugars using two different fluoroaryl borane catalysts, B(C6F5)3 and B(3,5-CF3)2C6H3)3 (BAr3,5-CF3).

For example, persilylated 2-deoxyglucose shows exocyclic C–O bond cleavage/reduction with the less sterically congested BAr3,5-CF3 catalyst, whereas endocyclic C–O bond cleavage/reduction predominates with the more Lewis acidic B(C6F5)3.

From biomass, which provides a limited number of viable feedstocks/starting materials, high value products can be selectively synthesized by the choice of catalysts.