Nonmetal-Catalyzed Iodination of Arenes with Iodide and Hydrogen Peroxide
Jernej Iskra*, Stojan Stavber, Marko Zupan
*Laboratory for Organic and Bioorganic Chemistry, Jozef Stefan Institute and
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Jamova
39, 1000 Ljubljana, Slovenia, Email: jernej.iskra
ijs.si
J. Iskra, S. Stavber, M. Zupan, Synthesis, 2004, 1869-1873.
DOI: 10.1055/s-2004-829136
Abstract
A selective and efficient oxidative iodination of electron rich arenes was carried out with one equivalent of KI and two equivalents of 30% hydrogen peroxide in MeOH in the presence of strong acid.
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Details
The document discusses a study on the nonmetal-catalyzed iodination of arenes using potassium iodide (KI) and hydrogen peroxide (H2O2) in methanol (MeOH) with the addition of sulfuric acid (H2SO4). This method aims to provide a green and efficient alternative to traditional halogenation processes, which often involve hazardous molecular halogens. The researchers found that adding H2SO4 was crucial to prevent the decomposition of H2O2 and to promote the iodination reaction. Various substituted arenes, including anisoles, phenols, and anilines, were successfully iodinated with high yields and regioselectivity. The study demonstrated that the method is effective for a wide range of aromatic compounds, producing mono- and di-iodinated products without the need for metal catalysts. The process is eco-friendly, generating only water as a byproduct. The document includes detailed experimental procedures, reaction conditions, and characterization data for the iodinated products. The research highlights the potential of this method for applications in pharmaceutical and agricultural chemistry, where halogenated organic molecules are valuable intermediates.
Key Words
iodination, haloperoxidation, hydrogen peroxide, oxidative halogenation, aromatics
ID: J66-Y2004-2250
