Truce‐Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids

Abstract

The Truce‐Smiles rearrangement is an intramolecular SNAr 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.