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 K 3 PO 4 and a catalytic amount of CuCl at room temperature, followed by treatment with N -iodosuccinimide and BF 3 ·OEt 2 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, K 2 CO 3, 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, Ag 2 CO 3, and K 2 S 2 O 8; and 3-iodo-2-(2′,5′-dioxan-1′-yl)-4-phenylquinoline with benzoyl peroxide in dioxane.