An efficient and facile iodine-catalysed approach has been established for the formation of α-substituted aryl ketones and valuable substituted naphthofurans. Under the same reaction conditions, a series of highly functionalized pyrroles could be readily obtained. This metal-free and environmentally friendly reaction proceeded very well and delivered the products in good to excellent yields. This work highlights the formation of α-substituted aryl ketones, naphthofuran and pentasubstituted pyrrole derivatives under catalytic amount of iodine in one-pot fashion, demonstrating the broad substrate scope.