Regioselective Trifluoromethylation via Activation of PyridinesRegioselective Trifluoromethylation via Activation of Pyridines

2020 Fiscal Year Final Research Report

• Project/Area Number: 18K14222
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Yamaguchi University
• Principal Investigator: Kawamoto Takuji 山口大学, 大学院創成科学研究科, 助教 (70756139)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Keywords: ラジカル / トリフルオロメチル

Outline of Final Research Achievements

We developed The one-pot triflation/radical trifluoromethylation/triflation of imines leading to CF3-substituted vinyl trifluoromethanesulfonyl amides. The reaction proceeds via the radical trifluoromethylation of vinyl trifluoromethanesulfonyl amides as the key step. This reaction is suitable for a variety of imines having halogen atoms, electron-donating groups, and electron-withdrawing groups in moderate to good yields. Vinyl trifluoromethanesulfonyl amides can act as bifunctional reagents, whereby they serve as the trifluoromethyl radical source and radical acceptor.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

トリフルオロメチル基を有機分子に導入すると化合物の代謝安定性，脂溶性，生物学的利用能が向上する。そのため，これまでにトリフルオロ基を有する様々な 医薬品が開発されている。本研究では，ビニルトリフルオロメタンスルホニルアミドを用いる新しいトリフルオロメチル化反応を開発した。得られた化合物は医農薬への応用が期待できる。