Iodination of Aryltrimethylsilanes: A Mild Approach to Iodophenylalanine

Article abstract of DOI:10.1021/jo00375a015

Phenylalanine has been labeled with the radioactive isotopes of iodine by using harsh conditions or toxic mercury compounds.A mild method of incorporating iodine onto an aryl ring was developed that combines two methods that have been used separately for the production of aryl iodides: (1) the use of the Lewis acid to activate the elecrophile, I2, and (2) the use of a trimethylsilyl group to direct the introduction of iodine.Simple aryltrimethylsilanes and a phenylalanine-containing peptide were successfully iodinated by this method.