80331-28-8Relevant academic research and scientific papers
Palladium-Catalyzed Conjugate Addition Type Reaction of Aryl Iodides with α,β-Unsaturated Ketones
Cacchi, S.,Arcadi, A.
, p. 4236 - 4240 (2007/10/02)
Aryl iodides have been found to react with α,β-unsaturated ketones in the presence of catalytic amounts of palladium, an excess of formic acid, and triethylamine, giving rise to conjugate addition type products.The electron-withdrawing power of the group attached to the olefinic double bond, the substituent β to the carbonyl group, and the basic reaction medium appear to effect greatly the conjugate addition/vinylic substitution ratio.
THE PALLADIUM-CATALYSED CONJUGATE ADDITION TYPE REACTION OF ARYLMERCURY COMPOUNDS WITH α,β-UNSATURATED KETONES IN A TWO-PHASE SYSTEM
Cacchi, S.,Misiti, D.
, p. 2941 - 2946 (2007/10/02)
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.
