高价碘介导的 N-烯丙基羧酰胺电化学氟环化合成 2-恶唑啉
Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator.
作者信息
Haupt John D, Berger Michael, Waldvogel Siegfried R
机构信息
Institute of Organic Chemistry , Johannes Gutenberg University Mainz , Duesbergweg 10-14 , 55128 Mainz , Germany.
出版信息
Org Lett. 2019 Jan 4;21(1):242-245. doi: 10.1021/acs.orglett.8b03682. Epub 2018 Dec 17.
A resource saving protocol for the synthesis of 5-fluoromethyl-2-oxazolines by using electrochemistry has been realized. Thereby, a hypervalent iodine species I(III) is generated by anodic oxidation in the presence of EtN·5HF and mediates the cyclization of N-allylcarboxamide to 5-fluoromethyl-2-oxazoline. This method allows application to various substrates furnishing the 2-oxazolines with yields up to 68%. The protocol is easy to conduct under constant current conditions offering a sustainable alternative over conventional reagent-based pathways.
已经实现了一种通过电化学合成5-氟甲基-2-恶唑啉的资源节约型方案。由此，在EtN·5HF存在下通过阳极氧化产生高价碘物种I(III)，并介导N-烯丙基甲酰胺环化生成5-氟甲基-2-恶唑啉。该方法适用于各种底物，可提供产率高达68%的2-恶唑啉。该方案在恒流条件下易于实施，为传统的基于试剂的途径提供了一种可持续的替代方法。
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