Catalysis

Phosphine

Ketone

Receptor

Palladium

Ylide

Alkyl

Biochemistry

Medicinal chemistry

Combinatorial chemistry

Ligand (biochemistry)

Organic chemistry

Chemistry

Aryl

Organic Letters

Ylide-functionalized phosphine (YPhos) ligands allow the palladium-catalyzed α-arylation of alkyl ketones with aryl chlorides with record setting activity. Using a cyclohexyl-substituted YPhos ligand, a wide range of challenging ketone substrates was efficiently and selectively monoarylated under mild conditions. A newly designed YPhos ligand bearing tert-butyl groups on the coordinating phosphorus atom is already active at room temperature. The synthetic potential was demonstrated by gram-scale reactions and the succinct synthesis of ε-caprolactone derivatives.

Ylide-Functionalized Phosphine (YPhos)–Palladium Catalysts: Selective Monoarylation of Alkyl Ketones with Aryl Chlorides