A simple and efficient iron-catalyzed divergent dehydrative coupling of carbazoles and benzylic alcohols has been developed. By using different iron catalysts, mono-substituted or di-substituted carbazole-based di-/triarylmethanes, some of which are bioactive and potential pharmaceutical molecules or potential molecular precursors for optoelectronic materials, were synthesized site-selectively from the same set of reactants. This method was demonstrated with 68 examples, in up to 98% yield and with broad functional group compatibilities.