Recently, organometallic transformations have been pursued with renewed interest to approach the elusive addition reaction of the NÀH bond across alkynes. [1] As a cleaner alternative to the use of metal-containing reagents and catalysts we have developed useful reactions for CÀC bond formation and cleavage, based on the iodinating reagent bis(pyridine)iodonium(i) tetrafluoroborate (IPy 2 BF 4 ). [2] Herein, we present a powerful intramolecular addition of aniline and of several of its Nderivatives to alkynes, which relies on a simple iodination process. This new reaction entails a novel approach, and results in a general and valuable entry to the biological and synthetically relevant indole core. [3,4] We have previously established a robust iodination of anilines that leads to the synthesis of substituted indoles via CuI-mediated cyclization of the corresponding o-((trimethylsilyl)ethynyl)aniline derivatives. [5] Certainly, new processes that selectively place additional functionality at the time of assembling the indole core are highly desirable. [6] Now, we illustrate a direct and clean entry to valuable 2-substituted-3-iodoindoles from readily available precursors. Thus, N-protected o-(alkynyl)anilines 1 furnish N-protected 3-iodoindoles 2 upon reaction with IPy 2 BF 4 , [2] the iodinating agent of choice to promote this process [7] (Scheme 1).