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Intermolecular Dearomative 1,2‐Amination/Carbonylation via Nucleophilic Addition of Simple Amines to Arene π‐Bonds

Zheng Jian Li, Ming‐Yang Wang, Chuqiao Li, Wei‐Long Zeng, Wei Li

2023Chemistry - A European Journal17 citationsDOIOpen Access PDF

Abstract

Abstract The incorporation of the privileged amino functionality is of paramount importance in organic synthesis. In contrast to the well‐developed amination methods for alkenes, the dearomative amination of arenes is largely underexplored due to the inherently inert reactivity of arene π‐bonds and selectivity challenges. Herein, we report an intermolecular dearomative aminofunctionalization via direct nucleophilic addition of simple amines to chromium‐bound arenes. This multicomponent 1,2‐amination/carbonylation reaction enables rapid access to complicated alicyclic compounds containing amino and amide functionalities from benzene derivatives under CO‐gas‐free conditions, which also represents the first application of nitrogen‐based nucleophiles in η 6 ‐coordination‐induced arene dearomatizations.

Topics & Concepts

AminationChemistryNucleophileCarbonylationReactivity (psychology)AmideOrganic chemistryIntermolecular forceSelectivityCombinatorial chemistryReductive aminationMedicinal chemistryMoleculeCatalysisPathologyAlternative medicineCarbon monoxideMedicineCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic ChemistrySynthesis and Catalytic Reactions
Intermolecular Dearomative 1,2‐Amination/Carbonylation via Nucleophilic Addition of Simple Amines to Arene π‐Bonds | Litcius