Solvent‐free diazotization–azidation of aryl amine using a polymer‐supported azide ion

Abstract

Crosslinked poly (4-vinylpyridine)-supported azide ion was used as an effective azidating agent for deazodination of stable arenediazonium salts under solvent-free conditions in high yields. The diazotization of aromatic amines was prepared by grinding the combination of an aromatic amine, sodium nitrite (NaNO 2 ), p-toluene sulfonic acid (p-TsOH), and 0.2 mL H 2 O in a mortar. Grinding was continued for deazodination-azidation of the obtained relatively stable diazonium salts, with addition of crosslinked poly (4-vinylpyridine) supported azide ion to obtain the corresponding aryl azides. The spent polymeric reagents can usually be removed and regenerated.

Arenediazonium salts transformations in water media: Coming round to origins

“…Thus, poly-(4-vinylpyridine)-supported azide [P4-VP]N3 has been used for preparation of aryl azides from anilines via onepot generation of arenediazonium tosylates under solvent-free conditions (Scheme 7) [27].…”

A reliable one-pot synthesis of aryl azides from aryl amines using organotin azides as effective and recoverable reagents

“…Therefore, several protocols have been developed with the aim to improve both the efficiency and usefulness of the classical diazotization-azidodediazoniation route. Among these, neutral conditions [5], neutral and mild conditions with non-hazardous reagents [6], reusable ionic liquids as solvents [7], water media [8], stable diazonium salts intermediates [9], continuous flow processes [10] and polymer-supported diazotizing [11] or azidating [12] reagents, are a few of the implemented strategies.…”