Photocatalytic C–Si Bond Formations Using Pentacoordinate Silylsilicates as Silyl Radical Precursors: Synthetic Tricks Using Old Reagents
Yumo Zhao, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang
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.
Topics & Concepts
SilylationChemistryHydrosilylationReagentPhotocatalysisSolventPhotochemistryReactivity (psychology)Broad spectrumVisible spectrumCatalysisOrganic chemistryCombinatorial chemistryOptoelectronicsAlternative medicineMedicinePathologyPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods