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Ruthenium‐Catalyzed Activation of Nonpolar C−C Bonds via π‐Coordination‐Enabled Aromatization

Lun Xu, Hang Shi

2023Angewandte Chemie International Edition11 citationsDOI

Abstract

Activation of C-C bonds allows editing of molecular skeletons, but methods for selective activation of nonpolar C-C bonds in the absence of a chelation effect or a driving force derived from opening of a strained ring are scarce. Herein, we report a method for ruthenium-catalyzed activation of nonpolar C-C bonds of pro-aromatic compounds by means of π-coordination-enabled aromatization. This method was effective for cleavage of C-C(alkyl) and C-C(aryl) bonds and for ring-opening of spirocyclic compounds, providing an array of benzene-ring-containing products. The isolation of a methyl ruthenium complex intermediate supports a mechanism involving ruthenium-mediated C-C bond cleavage.

Topics & Concepts

RutheniumAromatizationChemistryCatalysisBond cleavageArylRing (chemistry)BenzeneAlkylCleavage (geology)StereochemistryPhotochemistryMedicinal chemistryOrganic chemistryMaterials scienceFracture (geology)Composite materialCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions
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