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

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.

Automated summary

A visible-light-induced photocatalytic C-Si formation strategy was developed using Martin's spirosilane-derived pentacoordinate silylsilicates as silyl radical precursors. The strategy exhibited efficient hydrosilylation of a wide range of alkenes and alkynes, as well as C-H silylation of heteroarenes. Notably, Martin's spirosilane was stable and could be easily recovered. Moreover, the reaction performed well using water as the solvent or low-energy green LEDs as an alternative energy source.