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

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posted on 11.01.2019, 00:00 by Anastasia I. Govdi, Natalia A. Danilkina, Alexander V. Ponomarev, Irina A. Balova
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.