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Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations

Liang Hao, Lujun Wang, Yun‐Xing Ji, Han Wang, Bo Zhang

2020Angewandte Chemie16 citationsDOI

Abstract

Abstract The first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral reaction conditions is reported. The practical protocol employs commercially available and cheap NHPI as a hydrogen‐atom transfer (HAT) mediator and operates at room temperature with high selectivity, leading to various valuable silanols in moderate to good yields. Notably, this electrochemical method exhibits a broad substrate scope and high functional‐group compatibility, and it is applicable to late‐stage functionalization of complex molecules. Preliminary mechanistic studies suggest that the reaction appears to proceed through a nucleophilic substitution reaction of an electrogenerated silyl cation with H 2 O.

Topics & Concepts

SilylationChemistryElectrochemistryNucleophileSurface modificationNucleophilic substitutionHydrolysisSubstrate (aquarium)SelectivityMoleculeCombinatorial chemistryHydrogen atomInorganic chemistryPhotochemistryOrganic chemistryCatalysisPhysical chemistryGroup (periodic table)ElectrodeOceanographyGeologyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods