Zirconium-mediated selective synthesis of 1,4-dialkyl(aryl)-hexa-substituted benzenes from two silyl-substituted alkynes and one internal alkyne

Abstract

Based on the formation of 2,5-bis(trimethylsilyl)-zirconacyclopentadienes from two silylalkynes with Cp₂ZrBu₂ and the Cu-mediated formation of 1,4-disilylbenzene via the cycloaddition of zirconacyclopentadienes to disubstituted alkynes, a selective synthesis of 1,4-dialkyl(aryl)-hexa-substituted benzenes was achieved followed by iodination and coupling reaction. The coupling reactions were carried out with either organolithium reagent or organozinc reagent(Negishi coupling), depending on the electrophilic species.

Keywords

Zirconium / Hexa-substituted benzene / Iodination / Coupling reaction

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