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

• DOI: 10.1021/acs.orglett.0c01780
• Publication Date: 2020-06-23T13:14:56Z
• Authors: Xiaoming Xu; Ying Zhong; Qingzhao Xing; Ziwei Gao; Jing Gou; Binxun Yu
• Keywords: Furan; Triazole

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