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

摘要

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.