Synlett 2015; 26(09): 1145-1152
DOI: 10.1055/s-0034-1380458
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 21 December 2014

Accepted after revision: 20 January 2015

Publication Date:
04 March 2015 (online)

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.

 
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