Efficient α-Iodination of Carbonyl Compounds Under Solvent-Free Conditions Using Microwave Irradiation

Abstract

Direct conversion of carbonyl compounds into α-iodocarbonyl compounds has been successfully achieved under solvent-free microwave irradiation conditions using N-iodosuccinimide and p-toluenesulfonic acid.

carbonyl - halides - iodine - ketones - microwave

References

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<A NAME="RU01003ST-16">16</A>

General experimental procedure: A neat mixture of ketone, NIS (1.2 equiv), and p-toluenesulfonic acid monohydrate (1.2 equiv) was placed in a glass test tube. The test tube containing reaction mixture was inserted in an alumina bath inside a household microwave oven and irradiated (700 W) three to four times for a period of 20 s with 10 s interval. After cooling down, the reaction mixture was extracted with dichloromethane (2 × 25 mL) and washed with water (40 mL). The dichloromethane layer was separated and dried over MgSO₄. After evaporation of the solvent, the residue was purified by flash column chromatography (SiO₂, dichloromethane) to give pure α-iodoketone.