Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Brønsted acids enable the effective Friedel− Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo-[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-farundescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge. Article pubs.acs.org/joc