Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne

doi:10.1007/s40242-016-6071-0

Abstract

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.

Key words: Zirconium, Hexa-substituted benzene, Iodination, Coupling reaction

LI Junqiu, ZHANG Jiqian, QU Hongmei, LIU Jun, LI Juan, ZHOU Lishan. Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne[J]. Chemical Research in Chinese Universities, 2016, 32(3): 366-372.

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