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Zirconium-Mediated Synthesis of Multi-substituted dibenzosilole and Benzonaphthosilole derivatives

Transactions of Tianjin University 2018年第6期24卷 538-546页

作者： Hongmei Qu Xin Zhang Xu Chen Hui Zhang Yican Men Junqiu Li Key Laboratory of Systems Bioengineering (Ministry of Education) School of Chemical Engineering and TechnologyTianjin University Tianjin Kingsrial S&T Co. Ltd

In this study, a new zirconium-mediated cycloaddition for preparing dibenzosilole derivatives was developed using siliconbridged diynes and electron-withdrawing alkynes as starting materials. The preparation of silicon-bridged diynes from 1-bromide-2-iodobenzene, terminal alkynes, and dimethyldichlorosilane was also studied. Unlike in the previous synthesis methods, much higher yields of electron-withdrawing group-substituted dibenzosilole derivatives were obtained. In addition, a new synthesis strategy for preparing benzonaphthosilole derivatives using internal alkynes, 1,4-dibromobenzene, and electron-withdrawing alkynes as starting materials is proposed. Compared with previous methods, alkyl, phenyl, and electron-withdrawing groups can be successfully introduced onto aromatic rings, and the positions of these substituents can be easily controlled. The cycloaddition reactions for dibenzosilole and benzonaphthosilole derivatives are highly efficient one-pot processes, and the raw materials are available and easily prepared. Using these new methods, a series of novel multisubstituted dibenzonsilole and benzonaphthosilole derivatives were obtained effectively.

关键词： Zirconium-mediated reactions dibenzosilole derivatives Benzonaphthosilole derivatives Multi-substitution

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