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. 2025 Feb 17;64(8):e202422442.
doi: 10.1002/anie.202422442. Epub 2025 Jan 28.

The Electrochemical Iodination of Electron-Deficient Arenes

Sara Torabi  1 , Mahdi Jamshidi  1 , Gerhard Hilt  1
Affiliations

The Electrochemical Iodination of Electron-Deficient Arenes

Sara Torabi et al. Angew Chem Int Ed Engl. .

Abstract

The iodination of electron-deficient arenes and heteroarenes is a long-standing problem in organic synthesis. Herein we describe the electrochemical iodination in nitromethane with Bu4NI as iodine source and supporting electrolyte under Lewis acid-free conditions in the presence of small amounts of chloride anions. The electrochemically generated reagent could be applied for the iodination of halogenated arenes, aromatic aldehydes, acids, esters, ketones, as well as nitroarenes to afford the products in good to excellent yields.

Keywords: electrochemistry; electron-deficient arenes; interhalogen compounds; iodination; regioselectivity.

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References

    1. For a recent review on new developments in cross-coupling reactions, see: A. Sen, Y. M. A. Yamada, Synthesis 2024, 56 and references therein.
    1. None
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    1. Y. Liu, P. Li, Y. Wang, Y. Qui, Angew. Chem. Int. Ed. 2023, 62, e202306679;
    1. L. Ding, Y. Zhao, H. Lu, Z. Shi, M. Wang, Angew. Chem. Int. Ed. 2023, 63, e202313655;

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