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Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions

2018; Elsevier BV; Volume: 59; Issue: 8 Linguagem: Inglês

10.1016/j.tetlet.2018.01.038

1873-3581

Rafaela Gomes Martins da Costa, Francisco R. L. Farias, Davi F. Back, Jones Limberger,

Synthesis and Biological Evaluation

A useful protocol for arylation of the olefin double bond of chalcones to afford tri- and tetra-substituted chalcone derivatives is reported. The protocol begins with the Heck reaction between chalcones and aryl iodides providing β-arylchalcones. This reaction tolerates various functional groups on both rings, as well as deactivated aryl iodides. The products are obtained in moderate to excellent yields and the (E)-β-arylchalcones (E:Z > 96:4) can be isolated via precipitation. Competitive Heck reactions pointed to a significant effect of ring one substituents on the reaction rate, while substituents on ring two have a much smaller effect. To access α,β-diarylchalcones, a sequential bromination-Suzuki cross coupling strategy was applied to the β-arylated compounds which afforded double arylated chalcone derivatives in 60–99% yield over two steps.