Further studies on the iodination of aryltrimethylsilanes

Article abstract of DOI:10.1055/s-1993-25912

Aryltrimethylsilanes can be readily iodinated using iodine monochloride and a silver salt in methanol. This procedure works well with aromatic rings that contain a deactivating group and is compatible with sensitive functional groups. To illustrate this a carbobenzyloxy protected 4-trimethylsilylphenylalanine ester was iodinated in good yield. The use of iodine monochloride instead of iodine results in faster reaction times than previously reported and reduced the waste of iodine, which would be beneficial in procedures where the use of other isotopes of iodine would be desired. Careful choice of solvents also allows the monoiodination of 1,4-bis(trimethylsilyl)benzene in good yield, which could prove useful in the synthesis of novel arylsilanes.