THE PALLADIUM-CATALYSED CONJUGATE ADDITION TYPE REACTION OF ARYLMERCURY COMPOUNDS WITH α,β-UNSATURATED KETONES IN A TWO-PHASE SYSTEM

Article abstract of DOI:10.1016/S0040-4020(01)92369-5

Pd-catalysed reaction of arylmercury compounds with α,β-enones in an acidic two-phase system provides a mild and selective way to β-aryl ketones.The present conjugate addition type reaction may accomodate a wide variety of functional groups.Thus, aryl units containing electron-donating and electron-withdrawing substituents such as -Me, -Cl, -CHO, -COMe, -COOMe, -COOH, -OH, -OMe, -NHCOMe and NO2 were succesfully transfered to the β C atom of benzalacetone.A number of α,β-enones were also treated with 3-formylphenyl mercury chloride to give the corresponding β-(3-formylphenyl) derivatives.The main limitation seems to arise from steric hindrance in the starting α,β-enonic system.Substituents in the aryl moiety of the organomercury compounds were found to affect the transmetalation steps in the direction expected for a rate determining ?-complex formation.