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Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization

Lixia Liu, Cong‐Ying Zhou, Chengming Wang

2022Green Synthesis and Catalysis17 citationsDOIOpen Access PDF

Abstract

A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported. This protocol provides an efficient access for highly congested quaternatry carbon centers construction. It also features operationally simplicity, mild reaction conditions and good functional group tolerance. Moreover, the reported procedure can be easily emplified to 1 ​g scale. Mechanism study reveals the dearomative transformation possibly undergoes a single electron transfer process with NHC radical cation as a reactive intermediate.

Topics & Concepts

Hypervalent moleculeReagentChemistryCatalysisCombinatorial chemistryFunctional groupRedoxReactive intermediateOrganic chemistryPolymerN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions