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Updated: Jul 30, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Truce-Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids
Yu Wang1, Wanying Pan1, Yuxuan Zhang1
1Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, Department of Fine Chemistry and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, P. R. China.
Abstract:
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.
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