Using the previously described method by Zhang et al. (Scheme 1a), we envisaged the synthesis of compounds 6 with an acyl-fluorous tag, introduced by replacement of one of the N-bound alkyl substituents R in compound 4. The desired F-tagged alkynylfunctionalized aniline precursors 15a-15u were obtained from 2-iodoaniline (9) through a three-step procedure (Scheme 2). The order of the reaction steps and the conditions were varied in the attempt to optimize the outcome of the target compounds. Scheme 2