Govdi Anastasia I, Danilkina Natalia A, Ponomarev Alexander V, Balova Irina A
Institute of Chemistry , Saint Petersburg State University (SPbU) , Universitetskaya nab. 7/9 , Saint Petersburg 199034 , Russia.
J Org Chem. 2019 Feb 15;84(4):1925-1940. doi: 10.1021/acs.joc.8b02916. Epub 2019 Jan 31.
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.
发现以三（三苯基膦）碘化亚铜为催化剂，使碘代二乙炔与有机叠氮化物进行铜催化的1,3 - 偶极环加成反应是合成5 - 碘代 - 4 - 乙炔基三唑的一种高效一步合成路线。该反应对丁二炔和叠氮部分的各种官能团具有耐受性。还评估了所得到的5 - 碘代 - 4 - 乙炔基三唑的合成应用：其与炔烃的Sonogashira偶联反应生成了不对称取代的三唑稠合烯二炔体系，而铃木反应则得到了相应的5 - 芳基 - 4 - 乙炔基三唑。
