An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
Adriano Bauer, Giovanni Di Mauro, Jing Li, Nuno Maulide
Abstract
The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.
Topics & Concepts
UmpolungNucleophileChemistryReactivity (psychology)CyclopropanationKetoneCarbocationReagentCationic polymerizationOrganic chemistryCatalysisPathologyMedicineAlternative medicineCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods