Lower Nitrogen Oxide Species as Catalysts in a Convenient Procedure for the Iodination of Aromatic Compounds

Article abstract of DOI:10.1021/jo00250a024

A simple method for the iodination of aromatic compounds, using I^- as the iodine source and the O2 and catalytic amounts of NO⁺BF4^- as the oxidant, is presented.The reactions are performed at 25 deg C in CF3COOH/CH2Cl2 or CF3COOH/CH3COOH mixtures and compounds with as different reactivities as the halobenzenes and 1-methoxynaphthalene can be iodinated in very good yields.A set of relative rates, isotope effects, and isomer distributions in accordance with the electrophilic action of an "I⁺" species are presented.The formation of "I⁺" is discussed in terms of possible outer-sphere and inner-sphere electron-transfer steps.Aromatic bromination and to a lesser extent chlorination can be performed by using similar methods.