A novel intermolecular tandem oxidative aromatic coupling between arylidene fluorenes and unfunctionalized aromatics mediated by a DDQ/TFA oxidation system has been developed for the construction of 9,10-diarylphenanthrenes (DAPs). The formation of a benzylic carbocation species possessing a quaternary sp-carbon center on the fluorene moiety by an intermolecular oxidative Friedel-Crafts reaction of two different arenes successfully triggered the subsequent ring expansion to afford DAPs.
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