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-N2+Cl-, were obtained by the reaction between primary aryl amine and sodium nitrite in the presence of concentrated hydrochloric acid (HCl) at low temperature (05 degrees C). By ion exchange reaction between Ar-N2+Cl- with NaBF4, the stable arenediazonium tetrafluoroborates, Ar-N2+BF?4-, were prepared. Ar-N2+BF4-, were then converted to aryl iodides by crosslinked poly (4-vinylpyridine)-supported iodide, [P4-VP]I, in acetonitrile at room temperature. The spent polymeric reagent was regenerated and reused for several times without losing its activity. (C) 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012