The electrosynthesis of diaryliodonium salts

Abstract

The objective of this study was to investigate the electrosynthesis of diaryliodonium salts from the anodic oxidation of aryl iodides and arenes in an acid medium. The voltammogram of the solvent was recorded using a carbon rotation disc electrode. There was evidence of oxidation of the carbon electrode and/or intercalation of anions into the carbon.

The voltammograms of a series of aryl iodides and arenes were recorded at a carbon rotating disc electrode. It was seen that their oxidation potentials were dependent on the ring substituents. The aryl iodides had lower oxidation potential than the corresponding arene. The voltammogram of a diaryliodonium bisulfate was recorded at a vitreous carbon disc electrode and there was no evidence for the oxidation or reduction of the iodonium salt.

The cell conditions necessary for selective and efficient coupling of an aryl iodide and arene to give dimethyldiphenyliodonium salt were investigated. 4-Iodotoluene and toluene was adopted as the 'model' system. The isolated iodonium salts were seen to contain two isomers. A number of organic side products of the electrolysis were also identified.

A small series of symmetric, asymmetric and cyclic iodonium salts were successfully electrochemically synthesised, under constant current control, in order to demonstrate the generality of the electrolysis. The iodonium salts were isolated and characterised by NMR and mass spectroscopy.

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