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Silylacylation of Alkenes through N-Heterocyclic Carbene Catalysis

Huiwei Xu, Wanyao Zheng, Wen-Deng Liu, Yuqiao Zhou, Luqing Lin, Jiannan Zhao

2023Organic Letters24 citationsDOI

Abstract

The construction of silicon-containing molecules has received increasing attention in recent years. Herein, we report the generation of silyl radicals through NHC catalysis under mild reaction conditions. This methodology offers a novel and convenient route to a diverse range of β-silyl ketones with a broad substrate scope and good functional group compatibility. Both the radical clock and electrochemical studies are consistent with the hypothesis of ground-state SET, and a plausible mechanism for the organocatalytic transformation is proposed.

Topics & Concepts

SilylationChemistryCatalysisCarbeneRadicalCombinatorial chemistryScope (computer science)Compatibility (geochemistry)Substrate (aquarium)Functional groupMoleculeOrganic chemistryChemical engineeringComputer scienceOceanographyProgramming languageGeologyEngineeringPolymerN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods
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