Oxidative Rearrangement via 1,2-Aryl Migration using Hydroxy(tosyloxy)iodobenzene in a Polar Aprotic Solvent
Raj Kamal, Vipan Kumar, Ravinder Kumar, Sangeeta Saini, Rajesh Kumar
Abstract
A series of geminal β,β-ditosyloxy ketones were synthesized in moderate to good yields through hydroxy(tosyloxy)iodobenzene-mediated ditosyloxylation of readily accessible α,β-unsaturated ketones in a polar aprotic solvent. A mechanism has been proposed for the synthesis of the geminal β,β-ditosyloxy ketones, and entails an oxidative rearrangement involving a 1,2-aryl migration.
Topics & Concepts
IodobenzeneChemistryGeminalArylSolventOxidative phosphorylationPolarOrganic chemistryMedicinal chemistryCatalysisAstronomyBiochemistryPhysicsAlkylOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis