Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant
Francesca Foschi, Camilla Loro, Roberto Sala, Julie Oble, Leonardo Lo Presti, Egle M. Beccalli, Giovanni Poli, Gianluigi Broggini
Abstract
The palladium-catalyzed aminoazidation of aminoalkenes yielding azidomethyl-substituted nitrogen-containing heterocycles was developed. The procedure requires oxidative conditions and occurs at room temperature in the presence of hydrogen peroxide and NaN3 as the azide source. These conditions provide selective exo-cyclization/azidation of the carbon–carbon double bond, furnishing a versatile approach toward five-, six-, and seven-membered heterocyclic rings.
Topics & Concepts
ChemistryHydrogen peroxideCatalysisPalladiumIntramolecular forceAzideDouble bondPeroxideNitrogenCarbon fibersOrganic chemistryPhotochemistryCombinatorial chemistryComposite materialComposite numberMaterials scienceCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsClick Chemistry and Applications