Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles.,Organic Letters

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Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles.
Organic Letters ( IF 4.9 ) Pub Date : 2020-06-23 , DOI: 10.1021/acs.orglett.0c01780
Xiaoming Xu ₁ , Ying Zhong ₁ , Qingzhao Xing ₁ , Ziwei Gao ₁ , Jing Gou ₂ , Binxun Yu _{1,

3}

Affiliation

The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)₃ and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.

中文翻译：

Fur催化的基于呋喃脱芳香化的分子内[3 + 2]环加成反应，以构建熔融三唑。

含1,2,3-三唑的多环结构广泛存在于广泛的合成生物活性分子中，开发合成这些骨架的快速方法仍然是一项艰巨的任务。在这项工作中，描述了由生物质衍生的2-呋喃基甲醇与叠氮化物的催化环化反应，以形成稠合的三唑。该方法利用单一催化剂Yb（OTf）_3的优势，并通过糠基阳离子诱导的分子内[3 + 2]环加成/呋喃开环级联反应进行操作。

更新日期：2020-07-02

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