Selective Iodination of Alcohols with NaI/Amberlyst 15 in Acetonitrile

Abstract

A simple and effective procedure for conversion of primary, secondary, allylic and benzylic alcohols into the corresponding iodides is described using NaI/Amberlyst 15 in acetonitrile at room temperature. Selective conversion of benzylic alcohols in the presence of saturated alcohols into the corresponding benzylic iodides is achieved under these conditions.

Key words

iodination - Amberlyst 15 - benzylic alcohol - saturated alcohol - iodides

References

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24

General Procedure for the Conversion of Alcohols to Iodides (Table 1). To a stirred suspension of alcohol (1 mmol) and NaI (0.150 g, 1 mmol) in MeCN (10 mL) was added amberlyst 15 (H⁺-form, 1 g), and the resulting mixture was stirred at r.t. After completion of the reaction (TLC or GC), Et₂O (10 mL) was added and washed with aq sat. NaHCO₃ solution, followed by NaHSO₄. The resultant organic layer was extracted with Et₂O (3 × 10 mL) and the combined extract dried over anhyd Na₂SO₄. The solvent was removed under reduced pressure to afford iodides in almost pure form. If necessary, products were purified by column chromatography (eluent: hexane-EtOAc). The products were identified by IR, ¹H NMR, and GC.