Issue 19, 2025

Easy access to 5-cyanotriazoles via Pd-catalyzed cyanation of 5-iodotriazoles

Abstract

A straightforward approach for the attachment of a nitrile moiety to the 1,2,3-triazole core has been developed. The protocol is based on the cyanation of 5-iodo-1,2,3-triazoles which are readily accessible by Cu-catalyzed azide–iodoalkyne cycloaddition. Halogen substitution occurs smoothly with KCN as a cyanide source using a Pd(0)–Dpephos catalytic system. The reaction tolerates a variety of functional groups as well as some sensitive heterocyclic scaffolds and affords the target 5-cyano-1,2,3-triazoles in yields of up to 99%. Further transformations of the nitrile group enable an easy preparation of 1,2,3-triazoles bearing diverse moieties, including amides, amines, and some azaheterocycles.

Graphical abstract: Easy access to 5-cyanotriazoles via Pd-catalyzed cyanation of 5-iodotriazoles

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2025
Accepted
09 Apr 2025
First published
10 Apr 2025

Org. Biomol. Chem., 2025,23, 4725-4729

Easy access to 5-cyanotriazoles via Pd-catalyzed cyanation of 5-iodotriazoles

R. N. Galashev, G. V. Latyshev, Y. N. Kotovshchikov, N. V. Lukashev and I. P. Beletskaya, Org. Biomol. Chem., 2025, 23, 4725 DOI: 10.1039/D5OB00356C

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