Switchable Oxidative Reactions of <i>N</i>-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
Sabrina Giofrè, Manfred Keller, Leonardo Lo Presti, Egle M. Beccalli, L. Molteni
Abstract
as the oxidant resulted in an alkoxyacyloxylation process, with the formation of functionalized dihydro-1,4-benzoxazines. The reaction performed in the absence of palladium catalyst switched to an intramolecular Diels-Alder reaction (IMDA) pathway, which was the result of an oxidative dearomatization of the 2-aminophenol, nucleophilic addition, and Diels-Alder reaction cascade, highlighting the role of the oxidant as both a nucleophilic donor and an oxidizing agent.
Topics & Concepts
ChemistryIntramolecular forceCatalysisNucleophileOxidizing agentPalladiumMedicinal chemistryDiels–Alder reactionNucleophilic additionOxidative phosphorylationOxidative additionCombinatorial chemistryOrganic chemistryBiochemistryPhenothiazines and Benzothiazines Synthesis and ActivitiesCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions