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Updated: Jul 14, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
m-Iodosylbenzoic acid - a convenient recyclable reagent for highly efficient aromatic iodinations
Andreas Kirschning1, Mekhman S Yusubov, Roza Y Yusubova
1Institut für Organische Chemie and Zentrum für Biomolekulare Wirkstoffchemie (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany. andreas.kirschning@oci.uni-hannover.de
m-Iodosylbenzoic acid offers an efficient method for arene iodination at room temperature. The process allows for easy product purification and reagent recovery, making it a practical synthetic tool.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Arene iodination is a crucial transformation in organic synthesis.
- Developing efficient and environmentally friendly iodination methods is an ongoing challenge.
Purpose of the Study:
- To introduce a novel method for the direct iodination of arenes.
- To utilize m-iodosylbenzoic acid as an effective iodinating agent.
- To establish a convenient purification and reagent recovery protocol.
Main Methods:
- Reaction of arenes with iodine in the presence of m-iodosylbenzoic acid in acetonitrile.
- Purification of aryl iodides using ion exchange chromatography with IRA-900 (hydroxide form).
- Recovery of m-iodobenzoic acid by acidification of aqueous solutions or ion exchange resin.
Main Results:
- m-Iodosylbenzoic acid effectively mediates the iodination of arenes at room temperature.
- The developed method allows for facile separation of pure iodinated products.
- The reduced form of the reagent, m-iodobenzoic acid, is readily recoverable.
Conclusions:
- m-Iodosylbenzoic acid provides a convenient and efficient route for arene iodination.
- The integrated purification and recovery strategy enhances the practicality of this synthetic method.
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