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

The selective reduction of alpha,beta-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an alpha or beta 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 beta-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Automated summary

The selective reduction of alpha, beta-unsaturated carbonyl compounds to saturated carbonyl compounds was achieved using aqueous HI solution, with the introduction of an aryl group at the alpha or beta position improving yield. The reaction was applicable to compounds containing carboxylic acids and halogen atoms, and the mechanism involved Michael-type addition of iodide followed by reduction of the C-I bond through anionic and radical pathways.