Electricity Driven 1,3‐Oxohydroxylation of Donor‐Acceptor Cyclopropanes: a Mild and Straightforward Access to β‐Hydroxy Ketones
Debarshi Saha, Irshad Maajid Taily, Prabal Banerjee
Abstract
Abstract An unprecedented external oxidant‐free electrochemical protocol for 1, 3‐oxohydroxylation of donor‐acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π‐electron cloud of the aryl ring to cleave the strained C sp 3 −C sp 3 bond of cyclopropane to afford the β ‐hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.
Topics & Concepts
ChemistryCyclopropaneCyclic voltammetryAcceptorArylElectrochemistryRing (chemistry)Electron acceptorElectron donorStereochemistryPhotochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisElectrodeAlkylPhysical chemistryPhysicsCondensed matter physicsCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions