Iodination of Activated Aromatic Compounds Using Sodium Peroxodisulfate and Iodine: An Efficient Way to Iodinate Alkylated Calix[4]arenes

Abstract

A simple method for the iodination of activated arenes, using molecular iodine and sodium peroxodisulfate as the oxidant, is presented. The reaction is conducted in the presence of catalytic amounts of tetramethylammonium iodide as a phase-transfer catalyst in acetonitrile. For non-polar substances, which are not soluble in pure acetonitrile such as calix[4]arenes bearing long alkyl chains, a modified reaction is introduced. In this case the phase-transfer catalyst is changed to methyltriphenylphosphonium peroxodisulfate. Chloroform as a cosolvent mediates solubility. Furthermore, we show that the slightly basic conditions obtained upon the addition of sodium bicarbonate have a beneficial effect on the yield.

Key words

calixarenes - phase-transfer catalysis - iodination - oxidative halogenation - peroxides

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