Preparation of 3‑Iodoquinolines from N‑Tosyl-2-propynylamines with Diaryliodonium Triflate and N‑Iodosuccinimide

4-Aryl and 4-alkyl substituted 3-iodoquinolines could be smoothly obtained in one pot by treating N-tosyl-2-propynylamines with diaryliodonium triflate in the presence of K3PO4 and a catalytic amount of CuCl at room temperature, followed by treatment with N-iodosuccinimide and BF3·OEt2 at 0 °C, and then NaOH in methanol solution. The product, 3-iodo-4-phenylquinoline was smoothly transformed into 4-phenylquinoline with zinc; 4-phenyl-3-toluene­sulfenyl­quinoline with toluenethiol, K2CO3, and CuI; 4-phenyl-3-phenyl­ethynyl­quinoline with the Sonogashira coupling reaction; 4-phenyl-3-styryl­quinoline with the Heck coupling reaction; 3,4-diphenyl­quinoline with the Suzuki–Miyaura coupling reaction; 2-cyclohexyl-3-iodo-4-phenyl­quinoline with cyclo­hexane­carboxylic acid, Ag2CO3, and K2S2O8; and 3-iodo-2-(2′,5′-dioxan-1′-yl)-4-phenyl­quinoline with benzoyl peroxide in dioxane.