One-pot reduction of olefin and ketone moieties by a copper–phosphinecatalyst enabled by polar aprotic solvents

Abstract

One-pot reduction of both olefin and ketone moieties in a non-food biomass derived substrate using simple copper–phosphine catalysts is described. The electron rich, sterically unencumbered bis(diethylphosphino)ethane ligand used here gives an 84% yield of the product where both the olefin and ketone have been reduced in minutes using PhSiH₃ and dry acetonitrile as the solvent. The coordinating ability of acetonitrile appears to be critical for effecting this one-pot reduction. Labeling experiments indicate that ketone reduction in benzene occurs predominantly via a sigma bond metathesis pathway.