AROMATIC IODINATION WITH THE I-2-HGX(2) COMBINATION

The reaction of different aromatic compounds 1a-1t with iodine and a mercury(II)-salt 2 [mercury(II) chloride, nitrate or triflate] (1:1:1 molar ratio) in dichloromethane at room temperature leads to the corresponding iodoarene 3, the obtained regiochemistry being the expected. Concerning the mercury(II) salt, the observed reactivity decreased in the series triflate>nitrate>chloride according to their ionic character. An activation of the iodine molecule by the mercury(II) salt followed by a S-E reaction with the aromatic compound is postulated as the possible mechanism.