4.7 Article

The Ligand Free Palladium(II)-Catalyzed Regioselective 1,2-Addition of Enol Silanes to Quinones to Access 4-Hydroxy-4-(2-oxo-2-arylethyl)cyclohexadien-1-ones and Synthetic Applications

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 14356-14370

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00857

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Funding

  1. Syngene

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A regioselective 1,2-addition of silyl enol ethers to quinones can now be achieved via a palladium(II) enolate pathway, providing access to cyclohexadienone derivatives. This protocol proceeds under mild reaction conditions without the need for an external ligand or base, and the products have been used as synthetic precursors for fused heteroaryl systems.
In contrast to the conventional 1,4-addition process, regioselective 1,2-addition of silyl enol ethers to quinones can now be achieved via a palladium(II) enolate pathway that provides access to 4-hydroxy-4-(2-oxo-2-arylethyl)cyclohexa-2,5-dien-1-onederivatives. 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.

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