Fe-catalyzed tandem cross-dehydrogenative coupling of the methyl group in arylmethanes with 1,3-dicarbonyl compounds has been developed. The reaction affords one new C(sp3)鈥揅(sp2) bond and one new C(sp3)鈥揅(sp3) bond in a one-pot protocol. Further study suggests that this reaction might start with a Friedel鈥揅rafts-type reaction (cross-dehydrogenative arylation) followed by cross-dehydrogenative coupling with an activated methylene group under mild oxidative conditions.