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Oligosilanes as Silyl Radical Precursors through Oxidative Si−Si Bond Cleavage Using Redox Catalysis
Author(s) -
Yu Xiaoye,
Lübbesmeyer Maximilian,
Studer Armido
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011738
Subject(s) - hydrosilylation , silanes , silylation , radical , photochemistry , trimethylsilyl , chemistry , catalysis , silane , alkene , redox , bond cleavage , cycloaddition , polymer chemistry , materials science , organic chemistry
Oligosilanes are of great interest in the fields of organic photonics and electronics. In this communication, a highly efficient visible‐light‐mediated hydrosilylation of electron‐deficient alkenes through cleavage of a trimethylsilyl‐polysilanyl Si−Si bond is explored. These reactions smoothly occur on readily available organo(tristrimethylsilyl)silanes and other oligosilanes in the presence of an Ir III ‐based photo‐redox catalyst under visible light irradiation. Silyl radicals are generated through single electron oxidation of the oligosilane assisted by the solvent. The introduced method exhibits broad substrate scope and high functional group tolerance with respect to the organo(tristrimethylsilyl)silane and alkene components, enabling the construction of functionalized trisilanes. In addition, this catalytic system can be also applied to highly strained bicyclo[1.1.0]butanes as silyl radical acceptors.