Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system

Article abstract of DOI:10.1016/j.tetlet.2014.08.055

The novel reaction system comprising air/NH₄NO_3(cat.)/I₂/H₂SO_4(cat.)is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative α-iodination of aryl, heteroaryl, alkyl, and cycloalkyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved.