Chemoselective Reduction of α,β-Unsaturated Carbonyl and Carboxylic Compounds by Hydrogen Iodide

The selective reduction of α,β-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an α or β position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce β-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.