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Herein, Bi(OTf)3‐catalyzed Friedel‐Crafts‐type annulation of sulfonyl o‐hydroxyacetophenones with benzofused cycloethers is described. This single‐step strategy provides a variety of functionalized dibenzofused medium‐size (9–12) oxacycles through the formation of carbon‐carbon and carbon‐oxygen single bonds. Further, the oxidative application of target oxacycles was investigated. The chemical structures of the key products were determined based on the single‐crystal X‐ray analysis. In the overall process, water was generated as the byproduct.