Development of Regioselective C-H Trifluoromethylation

2017 Fiscal Year Final Research Report

• Project/Area Number: 16K13946
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Kyushu University
• Principal Investigator: Kuninobu Yoichiro 九州大学, 先導物質化学研究所, 教授 (40372685)
• Project Period (FY): 2016-04-01 – 2018-03-31
• Keywords: トリフルオロメチル化 / 位置選択的 / ヘテロ芳香族化合物 / Lewis酸－塩基相互作用 / Lewis酸 / 銅触媒 / トリフルオロメチルアニオン

Outline of Final Research Achievements

We succeeded in the development of the first 4-position-selective C-H trifluoromethylation of six-membered heteroaromatic compounds by electrophilically activating the six-membered heteroaromatic rings and sterically protecting the 2-position of the heteroaromatic rings.We developed copper-catalyzed 5-position-selective C-H trifluoromethylation of N-(8-quinolynyl)pivalamides. In addition, we succeeded in the inprovement of previously reported 2-position-selective C-H trifluoromethylation of six-membered heteroaromatic compounds. By using this reaction, a trifluoromethyl group can be introduced into the 2-position of quinoline derivatives in short reaction steps efficiently.

Free Research Field

有機合成化学、有機金属化学、有機材料化学