Teppei Sasaki, Katsuhiko Moriyama, Hideo Togo
JOURNAL OF ORGANIC CHEMISTRY 82(22) 11727-11734 2017年11月 査読有り
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 center dot OEt2 at 0 degrees 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-phenylethynyl-quinoline 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 cydohexarie-carboxylic acid, Ag2CO3, and K2S2O8; and 3-iodo-2-(2',5'-dioxan-1'-y1)-4-phenylquinoline with benzoyl peroxide in dioxane.