Modulating Electrostatic Interactions in Ion Pair Intermediates To Alter Site Selectivity in the C-O Deoxygenation of Sugars.

Controlling which products one can access from the predefined biomass-derived sugars is challenging. Changing from CH Cl to the greener alternative toluene alters which C-O bonds in a sugar are cleaved by the tris(pentafluorophenyl)borane/HSiR catalyst system. This increases the diversity of high-value products that can be obtained through one-step, high-yielding, catalytic transformations of the mono-, di-, and oligosaccharides.