Truce‐Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids
Yu Wang, Wanying Pan, Yuxuan Zhang, Limin Wang, Jianwei Han
Abstract
Ar reaction, enabling the formation of a new arene carbon-carbon bond with sufficiently strong carbon-centered nucleophile. Reported here are ortho-tosylmethylene functionalized diaryliodonium salts, which can undergo an unprecedented Truce-Smiles rearrangement in ionic liquids, resulting in sulfonyl-substituted ortho-iodo diarylmethanes as a powerful class of building blocks in chemical synthesis. The protocol features aryliodo moiety as a hyper nucleofuge, facilitating the formation of Meisenheimer complex within the migratory system.
Topics & Concepts
Smiles rearrangementMoietyIntramolecular forceNucleophileChemistryIonic bondingCarbon fibersIonic liquidSulfonylPhotochemistryIonMedicinal chemistryStereochemistryOrganic chemistryMaterials scienceCatalysisComposite numberAlkylComposite materialPhenothiazines and Benzothiazines Synthesis and ActivitiesOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions