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Photocatalytic Synthesis of Diarylmethyl Silanes via 1,6-Conjugate Addition of Silyl Radicals to <i>p</i>-Quinone Methides

Cong Luo, Wenhua Lu, Guoqin Wang, Zhengbing Zhang, Haiqiong Li, Pan Han, Dan Yang, Lin‐Hai Jing, Chen Wang

2022The Journal of Organic Chemistry27 citationsDOI

Abstract

A novel photocatalytic method for the preparation of diarylmethyl silanes was reported through silyl radicals addition strategy to p-QMs (p-quinone methides). This protocol could tolerate a variety of functional groups affording the corresponding silylation products with moderate to excellent yields. The resulting silylation products could be easily converted into a series of bioactive GPR40 agonists and useful p-QMs precursors for the synthesis of compounds possessing both quaternary carbon centers and silicon substituents through simple operation. A plausible mechanism of silyl radicals to p-QMs was proposed on the basis of experimental results and previous literature.

Topics & Concepts

SilylationSilanesChemistryRadicalOrganic chemistryPhotocatalysisCarbon fibersSiliconCatalysisSilaneComposite materialComposite numberMaterials scienceSynthesis of Indole DerivativesRadical Photochemical ReactionsSulfur-Based Synthesis Techniques