SELECTIVE IODODEAMINATION OF ELECTRON-DEFICIENT ANILINES USING TASK-SPECIFIC NITRITE- AND IODIDE-BASED IONIC LIQUIDS

A convenient and rapid method for the synthesis of aryliodides via the sequential diazotization-iodination of electron-deficient anilines using IL-ONO/[bmim]I is described. IL-ONO and [bmim]I were used as a nitrosonium source for diazotization of anilines and as a iodide ion source for subsequent iodination respectively. Electron-deficient anilines were efficiently and selectively iododeaminated in the presence of other anilines in good to excellent yields. This reaction can be regarded as a new method for the preparation of synthetically and pharmaceutically important iodoarens. Selectively iododeamination of electron-poor anilines in the presence of electron-rich anilines is one of the synthetically important advantages of this new method.