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A method to directly convert 2‐alkynylphenols to 3,4‐difunctionalized benzofurans and polycyclic benzofurans was developed. This protocol involves a hypervalent‐iodine‐mediated oxidative dearomatization to break the aromaticity of 2‐alkynylphenols, and a palladium‐catalyzed domino reaction to install two functional groups at the C3 and the C4 positions and restore the aromaticity of benzofurans.
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