Iodination of stable aromatic diazonium salt using crosslinked poly (4‐vinylpyridine)‐supported iodide

An efficient and simple method for the iodination of stable arenediazonium salts has been developed by using a polymer‐supported iodide. The arenediazonium chlorides, Ar‐N   2 + Cl − , were obtained by the reaction between primary aryl amine and sodium nitrite in the presence of concentrated hydrochloric acid (HCl) at low temperature (0–5°C). By ion exchange reaction between Ar‐N   2 + Cl − with NaBF 4 , the stable arenediazonium tetrafluoroborates, Ar‐N   2 + BF   4 − , were prepared. Ar‐N   2 + BF   4 − , were then converted to aryl iodides by crosslinked poly (4‐vinylpyridine)‐supported iodide, [P 4 ‐VP]I, in acetonitrile at room temperature. The spent polymeric reagent was regenerated and reused for several times without losing its activity. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012