Iron-Catalyzed Intermolecular Oxyamination of Terminal Alkenes Promoted by HFIP Using Hydroxylamine Derivatives
Georgina Kirby, Guillaume Prestat, Farouk Berhal
Abstract
An atom-economical intermolecular iron-catalyzed oxyamination of alkenes is described herein. The insertion of oxygenated and nitrogenated moieties from the hydroxylamine substrate was observed with full regio- and chemo-selectivity for terminal alkenes in good yields. HFIP as a solvent appeared to have a synergistic effect with the iron catalyst to promote the formation of the oxyaminated products. Preliminary mechanistic studies suggest a pathway going through an aziridination reaction followed by an in situ ring opening.
Topics & Concepts
HydroxylamineCatalysisChemistryIntermolecular forceSubstrate (aquarium)SelectivityRing (chemistry)SolventCombinatorial chemistryMedicinal chemistryOrganic chemistryMoleculeOceanographyGeologySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions