The Iodination of Strongly Electron-Deficient Arenes under Electrochemical Conditions with I2 and Catalytic Amounts of Chloride Anions

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Abstract
Dedicated to Prof. Dr. Gernot Frenking on the occasion of his 80th birthday. The electrochemical iodination of electron-deficient arenes beyond the hitherto described scope of such reactions performed with other iodinating agents is realized in a divided cell at a platinum anode in nitromethane utilizing I2 in stoichiometric amounts and catalytic amounts of Bu4NCl. The electrolysis generates the proposed reactive species [I2Cl]+ · CH3NO2 in the anode compartment (4.2 mA·cm−2) on a 0.25–1.00 mmol scale and leads to the desired meta-substituted iodinated products in high to excellent regioselectivities. For the iodination of dimethyl phthalate as electron-deficient arenes, which gave a mixture of products, the reactivity and the regioselectivity of the I2/Cl− system can be fine-tuned to a certain degree by addition of small amounts of Bu4NI, so that a unique variable electrochemical iodinating system could be established. Received: 19 December 2025 Accepted after revision: 11 February 2026 Article published online: 03 March 2026 © 2026. Thieme. All rights reserved. Georg Thieme Verlag KG Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
Funding Information
  • German Science Foundation (Hi655/20-1)

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