Friedel–Crafts-Type Reactions with Electrochemically Generated Electrophiles from Donor–Acceptor Cyclopropanes and -Butanes
Simon Kolb, Nils L. Ahlburg, Daniel B. Werz
Abstract
We describe a general electrochemical method to functionalize donor–acceptor (D–A) cyclopropanes and -butanes with arenes utilizing Friedel–Crafts-type reactivity. The catalyst-free strategy relies on the direct anodic oxidation of the strained carbocycles, which leads after C(sp3)–C(sp3) cleavage to radical cations that act as electrophiles for the arylation reaction. Broad reaction scopes in regard to cyclopropanes, cyclobutanes, and aromatic reaction partners are presented. Additionally, a plausible electrolysis mechanism is proposed.
Topics & Concepts
ChemistryElectrophileCyclobutanesElectrolysisFriedel–Crafts reactionElectrochemistryReactivity (psychology)Cleavage (geology)AcceptorCatalysisCombinatorial chemistryOrganic chemistryCycloadditionElectrodeEngineeringElectrolytePhysicsMedicineCondensed matter physicsPathologyGeotechnical engineeringAlternative medicinePhysical chemistryFracture (geology)Cyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions