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A palladium-catalyzed chelation-assisted C−H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C−H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.