Solvent‐ and Metal‐Free Chalcogenation of Bicyclic Arenes Using I₂/DMSO as Non‐Metallic Catalytic System

Abstract

We have developed a green and efficient protocol for the chalcogenation of bicyclic arenes by using I2/DMSO as catalytic system under solvent‐ and metal‐free conditions. This protocol allows access to several chalcogenated bicyclic arenes through C(sp2)–H bond functionalization, in good to excellent yields by using microwave irradiation or conventional heating.

KIO3‐Catalyzed C(sp2)‐H Bond Selenylation/Sulfenylation of (Hetero)arenes: Synthesis of Chalcogenated (Hetero)arenes and their Evaluation for Anti‐Alzheimer Activity

“…In another study, Lenardao used anilines and PhSeCl in glycerol under nitrogen atmosphere for the preparation of these compounds . Recently, we reported the oxidative C−Se/C−S bond formation of arenes through C(sp 2 )−H bond activation using I 2 /DMSO, under microwave irradiation –…”

A selenium-catalysed para-amination of phenols

“…However, no selenium-catalysed processes for the functionalisation of aromatic compounds have been developed. One challenge might be the electrophilic selenium catalysts react with the aryl rings directly, leading to the deactivation of catalyst 37 , 38 . We thought that a more nucleophilic site, to accommodate with selenium catalyst temporarily, might be helpful for competing with the deactivation.…”

NIS/TBHP Induced Regioselective Selenation of (Hetero)Arenes via Direct C−H Functionalization

“…So far, only several protocols have been established on the basis of this strategy, which are promoted by bases, iodide reagents oxidants or visible‐light; some of methods were completed under metal‐free conditions using only a half molar equiv. of diaryl diselenides (Scheme d) –. Considering atom economy and environment protection, establishment of novel methods for the selenation of (hetero)arenes via direct C−H functionalization using 0.5 equiv.…”