Iron‐Catalyzed Intramolecular Arene C(sp<sup>2</sup>)−H Amidations under Mechanochemical Conditions
Peng Shi, Yongliang Tu, Deshen Kong, Peng Wu, Ding Ma, Carsten Bolm
Abstract
-catalyzed intramolecular amidations lead to 3,4-dihydro-2(1H)-quinolinones in good to almost quantitative yields. The reactions do not require a solvent and are easy to perform. No additional ligand is needed for the iron catalyst. Both 4-substituted aryl and β-substituted dioxazolones provide products with high selectivity. Mechanistically, an electrophilic spirocyclization followed by C-C migration explains the formation of rearranged products.
Topics & Concepts
Intramolecular forceCatalysisElectrophileBall millSelectivityLigand (biochemistry)ChemistrySolventMedicinal chemistryArylCombinatorial chemistryStereochemistryOrganic chemistryMaterials scienceReceptorMetallurgyBiochemistryAlkylCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsChemical Synthesis and Analysis