Department of Medicinal Chemistry, BBRC, Syngene, Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bangalore 560009, India.
Department of Chemistry, Bharathidasan University, Palkalaiperur, Thiruchirapalli, Tamil Nadu 620024, India.
J Org Chem. 2021 Nov 5;86(21):14356-14370. doi: 10.1021/acs.joc.1c00857. Epub 2021 Sep 23.
In contrast to the conventional 1,4-addition process, regioselective 1,2-addition of silyl enol ethers to quinones can now be achieved a palladium(II) enolate pathway that provides access to 4-hydroxy-4-(2-oxo-2-arylethyl)cyclohexa-2,5-dien-1-one derivatives. This quinone alkylation protocol proceeds under mild reaction conditions at ambient temperature under open air and does not require either an external ligand for the palladium or the use of a base. Additionally, the cyclohexadienone products have been exploited as synthetic precursors for the construction of fused heteroaryl systems.
与传统的 1,4-加成过程相反，现在可以通过钯 (II) 烯醇化物途径实现硅基烯醇醚对醌的区域选择性 1,2-加成，从而获得 4-羟基-4-(2-氧代-2-芳基乙基)环己-2,5-二烯-1-酮衍生物。该醌烷基化反应在温和的反应条件下，在室温下、开放空气条件下进行，既不需要钯的外部配体，也不需要碱。此外，环己二烯酮产物已被用作构建稠合杂芳基体系的合成前体。
