Wilkinson's Catalyst - Catalytic Applications

Catalytic Applications

Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The mechanism of this reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively, followed by oxidative addition of H₂ to the metal. Subsequent π-complexation of alkene, intramolecular hydride transfer (olefin insertion), and reductive elimination results in extrusion of the alkane product, e.g.:

Other applications of Wilkinson’s catalyst includes the catalytic hydroboration of alkenes with catecholborane and pinacolborane, and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane. When the triphenylphosphine ligands are replaced by chiral phosphines (e.g., chiraphos, DIPAMP, DIOP), the catalyst becomes chiral and converts prochiral alkenes into enantiomerically enriched alkanes via the process called asymmetric hydrogenation.