Abstract
AbstractA simple, mild, and efficient method for the cyanation of stable arenediazonium salts was developed with polymer‐supported cyanide. Arenediazonium hydrogen sulfate (ArN2+HSO4−) was obtained by the reaction between a primary aryl amine and sodium nitrite in the presence of concentrated sulfuric acid (H2SO4) at low temperature (0–5°C). By an ion‐exchange reaction between ArN2+HSO4− and NaBF4, the stable arenediazonium tetrafluoroborate, ArN2+BF4−, was prepared. ArN2+BF4− was then converted to aryl nitrile with crosslinked poly(4‐vinylpyridine) supported cyanide ion in acetonitrile at room temperature. The spent polymeric reagent was regenerated and reused several times without any loss in its activity. This procedure offered advantages, including a higher isolated yield, shorter reaction time, and simple reaction workup. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012
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