Surfactant-Induced Substrate Selectivity in the Palladium-Nanoparticle-Mediated Chemoselective Hydrogenation of Unsaturated Aldehydes in Water

A hundred-fold substrate selectivity was observed in the competitive chemoselective hydrogenation of seven α,β-unsaturated aldehydes from C4 to C10 in water with palladium nanoparticles stabilized by sodium dodecyl sulfonate as the surfactant. The medium makes the longer lipophilic substrates hundreds of times more reactive than the shorter more hydrophilic ones, whereas in an organic medium almost no difference is observed.