Hypervalent‐Iodine‐Mediated Carbon–Carbon Bond Cleavage and Dearomatization of 9H‐Fluoren‐9‐ols

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A transition-metal-free synthesis of spiro compounds from 9H-fluoren-9-ols mediated by hypervalent iodine is reported. In this reaction, an unprecedented β-carbon elimination of tertiary alkoxyliodine(III) to form new diaryliodonium salts is proposed. The obtained phenol intermediates undergo oxidative dearomatization to furnish a class of oxo-spiro compounds. This domino reaction significantly increases the complexity of these molecules and shows excellent regio- and stereoselectivity.