Synthesis of <i>N</i>-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C–H Amination
Eric Falk, Valentina C. M. Gasser, Bill Morandi
Abstract
We report both an intermolecular C–H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.
Topics & Concepts
ChemistryAminationElectrophilic aminationIntramolecular forceReagentIntermolecular forceAlkylCatalysisFunctional groupElectrophileCombinatorial chemistrySalt (chemistry)Reaction conditionsOrganic chemistryMedicinal chemistryMoleculePolymerSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques