Nowadays, green chemistry plays an important role for environment. In this context, development of solvent-free ball milling or a grinding approach has attracted considerable interest in organic synthesis. Hence, carrying out a reaction under solvent-free conditions and at room temperature is an effective approach to eliminate the use of volatile organic compounds and to obtain the greenness in the process. On the other hands, pyrroles are the small aromatic, nitrogen-containing heterocyclic compounds present in many natural products. Pyrrole molecules show important biological relevance such as porphyrins, bile pigments, and coenzymes and are known to exhibit various applications as organic materials. In this work, we have presented a highly robust one-pot, four-component cascade cyclization reaction of α-keto aldehydes, anilines, activated alkynes, and aromatic nucleophiles to synthesize a diverse range of pharmaceutically important penta-substituted pyrroles. The reaction proceeded smoothly under ball-milling conditions in presence of iron catalyst.