Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles
Xiaoming Xu, Ying Zhong, Qingzhao Xing, Ziwei Gao, Jing Gou, Binxun Yu
Abstract
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.
Topics & Concepts
CycloadditionFuranIntramolecular forceChemistryCatalysisCombinatorial chemistryAzideRing (chemistry)TriazoleOrganic chemistryClick Chemistry and ApplicationsCyclopropane Reaction MechanismsSynthesis and Biological Evaluation