Abstract An efficient synthesis of N ‐methyl‐3‐chalcogeno‐indoles has been developed via iodine‐mediated electrophilic annulation reactions of 2‐alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2‐alkynylanilines selectively underwent the electrophilic annulation with numerous disulfides or diselenides leading to the corresponding 3‐sulfenylindoles and 3‐selenenylindoles in moderate to excellent yields. It is noteworthy that iron can promote the reaction.