The synthesis of iodolopyrazolium triflates via an oxidative cyclization of 3-(2-iodophenyl)-1H-pyrazoles is described. The reaction is characterized by a broad substrate scope, and various applications of these novel cyclic iodolium salts acting as useful synthetic intermediates are demonstrated, in particular in site-selective ring openings. This was finally applied to generate derivatives of the anti-inflammatory drug celecoxib. Their application as highly active halogen-bond donors is shown as well.