Catalytic Synthesis of π-Conjugated Silole through Si–C (sp3) Bond Activation

Qing-Wei Zhang; Kun An; Wei He

doi:10.1055/s-0034-1380458

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(09): 1145-1152
DOI: 10.1055/s-0034-1380458

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Catalytic Synthesis of π-Conjugated Silole through Si–C (sp³) Bond Activation

Qing-Wei Zhang

School of Medicine and Tsinghua-Peking Joint Centers for Life Science, Tsinghua University, Beijing 100084, P. R. of China eMail: whe@mail.tsinghua.edu.cn

,

Kun An

School of Medicine and Tsinghua-Peking Joint Centers for Life Science, Tsinghua University, Beijing 100084, P. R. of China eMail: whe@mail.tsinghua.edu.cn

,

Wei He*

School of Medicine and Tsinghua-Peking Joint Centers for Life Science, Tsinghua University, Beijing 100084, P. R. of China eMail: whe@mail.tsinghua.edu.cn

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Abstract

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Abstract

Conjugated siloles represent an important class of photoluminescence material. Traditional synthesis of siloles often suffered from low functional group compatibility due to the usage of stoichiometric organic lithium or magnesium reagents. In the past years, catalytic Si–C bond activation has emerged as a new strategy for the synthesis of siloles. For the benefit of this fast-developing research area, this article highlights the related pioneering work as well as our recent discovery of a tandem cyclization/Si–C (sp³) activation reaction that enables the rapid synthesis of indole- and benzofuran-conjugated siloles. We also discuss the reaction mechanism in greater detail.

Key words

silicon - rhodium - tandem reactions - metalation - chemoselectivity

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References and Notes

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