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(sp(3))-C(sp(2)) bond and one new C(sp(3))-C(sp(3)) bond in a one-pot protocol. Further study suggests that this reaction might start with a Friedel-Crafts-type reaction (cross-dehydrogenative arylation) followed by cross-dehydrogenative coupling with an activated methylene group under mild oxidative conditions.