One-pot preparation of heterocycles with diaryliodoniums under transition-metal-free conditions

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K05418
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Chiba University
• Principal Investigator: Togo Hideo 千葉大学, 大学院理学研究院, 教授 (60217461)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: ジアリールヨードニウム / クマリン / キノリン / クロメン / １工程合成反応 / 環化反応

Outline of Final Research Achievements

Treatment of 3-aryl-2-propyn-1-ols with diaryliodonium salts, followed by the reaction with NIS and BF3 gave 4-aryl-3-iodochromenes, treatment of N-tosyl 3-aryl-2-propynyl-1-amines with diaryliodonium salts, followed by the reaction with NIS and BF3 gave 4-aryl-3-iodoquinolines, and treatment of 3-aryl-2-propynoic acids with diaryliodonium salts, followed by the reaction with TBAB and Na2S2O8 gave 4-aryl-3-bromocoumarins in good yields, respectively. Those preparation methods are one-pot reactions of chromene, quinoline, and coumarin units. Moreover, those obtained 4-aryl-3-iodochromenes, 4-aryl-3-iodoquinolines, and 4-aryl-3-bromocoumarins were transformed to various 4-arylcoumarine derivatives and 4-arylquinoline derivatives by their oxidation, reduction, and coupling reaction with Pd complex.

Free Research Field

有機化学