The Truce-Smiles rearrangement is an intramolecular SN 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.
Keywords: Diaryliodonium Salt; Ion Pair; Ionic Liquid; Sulfonyl; Truce-Smiles Rearrangement.
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