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Photocatalytic C-Si Bond Formations Using Pentacoordinate Silylsilicates as Silyl Radical Precursors: Synthetic Tricks Using Old Reagents.

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A visible-light-induced photocatalytic C-Si formation strategy has been disclosed by uncovering the reactivity of Martin's spirosilane-derived pentacoordinate silylsilicates as silyl radical precursors. The hydrosilylation of a broad spectrum of alkenes… Click to show full abstract

A visible-light-induced photocatalytic C-Si formation strategy has been disclosed by uncovering the reactivity of Martin's spirosilane-derived pentacoordinate silylsilicates as silyl radical precursors. The hydrosilylation of a broad spectrum of alkenes and alkynes, as well as the C-H silylation of heteroarenes, has been demonstrated. Remarkably, Martin's spirosilane was stable and could be recovered via a simple workup process. Furthermore, the reaction proceeded well using water as the solvent or low-energy green LEDs as an alternative energy source.

Keywords: photocatalytic bond; silylsilicates silyl; pentacoordinate silylsilicates; radical precursors; silyl radical; bond formations

Journal Title: Organic letters
Year Published: 2023

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