Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts
Yulia А. Vlasenko, Thomas J. Kuczmera, Nikita S. Antonkin, Rashid R. Valiev, Павел С. Постников, Boris J. Nachtsheim
Abstract
Abstract Diaryliodonium salts are electrophilic arylation reagents in transition metal‐catalyzed and transition metal‐free reaction methods. Herein we present the application of azole‐stabilized diaryliodonium salts with additional thiophene‐2‐yl‐ligands as substrates for metal‐free nucleophilic arylations. Besides their synthesis, we demonstrate their application in chemoselective nitrations, oxygenations, aminations as well as thiolations under umpolung conditions. Convenient one ‐ pot procedures based on their in situ formation are also discussed. magnified image
Topics & Concepts
UmpolungChemistryAzoleNucleophileElectrophileReagentCombinatorial chemistryTransition metalRegioselectivityOrganic chemistryAntifungalCatalysisDermatologyMedicineCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions