Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
Camilla Loro, Marta Papis, Francesca Foschi, Gianluigi Broggini, Giovanni Poli, Julie Oble
Abstract
High Resolution Image Download MS PowerPoint Slide A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown to be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and sulfonamide nucleophiles to regioselectively afford 1-aryl-2-aminopropanes. The reaction is catalyzed by Cu(OTf) 2 and is expected to involve a Friedel–Crafts-type allylation of the arene, followed by hydroamination.
Topics & Concepts
HydroaminationSynthonArylChemistryCatalysisNucleophileAlcoholCascadeCombinatorial chemistryRegioselectivitySulfonamideMedicinal chemistryOrganic chemistryAlkylChromatographyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques