Oxidative iodination of arenes with manganese(IV) oxide or potassium permanganate as the oxidants

Article abstract of DOI:10.1246/bcsj.72.115

Novel and easy laboratory methods (novel Procedures 1-4) are presented for the oxidative mono- and diiodination of both activated and deactivated arenes, which gave the pure iodinated products in 62-89% yields. The reactions were carried out in the anhydrous, strongly acidic system, I₂/activated MnO₂/AcOH/Ac₂O/concd H₂SO₄, firstly at r.t. for 2 h, then at 45-55 °C for 2-9 h. The resulting mixtures were poured into excess aq Na₂SO₃ solution buffered with (NH₄)₂CO₃ to neutralize H₂SO₄. The following workups are given. Similarly, on carrying out the iodination reactions (at 35 °C, for one hour) in the anhydrous, strongly acidic system, I₂/KMnO₄/AcOH/Ac₂O/concd H₂SO₄, it was possible to mono- or diiodinate several deactivated arenes in 73-87% yields (improved Procedures 5 and 6).