Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole-Ligated Diaryliodonium Salts

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. (Figure presented.).