Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles.
2020
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.
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