Abstract
γ-Arylated γ, δ-unsaturated ketones have been prepared in good to excellent yields via the Pd-catalyzed Heck arylation of an electron-rich olefin, 5-hexen-2-one ( 1), with aryl bromides ( 2a– 2l) in the ionic liquid [bmim][BF 4]. The reaction is highly regioselective, leading predominantly to branched, γ-arylated products with Pd-DPPP [DPPP = 1,3-bis(diphenylphosphino)propane] catalysis. However, the choice of ligand is found to be crucial for regiocontrol; a change of ligand from DPPP to 1,1′-bis(diphenylphosphino)ferrocene (DPPF) affords predominantly the ( E)-type, δ-arylated γ, δ-unsaturated ketones. The method is simple, effective, and applicable to the coupling of both electron-rich and electron-deficient aryl bromides with no need for any halide scavengers.
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