1‑Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4‑Ethynyl-5-iodo-1,2,3-triazoles

Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris­(tri­phenyl­phos­phine)­copper­(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne a...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-02, Vol.84 (4), p.1925-1940
Main Authors: Govdi, Anastasia I, Danilkina, Natalia A, Ponomarev, Alexander V, Balova, Irina A
Format: Article
Language:English
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Summary:Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris­(tri­phenyl­phos­phine)­copper­(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02916