Development of HF capturing asymmetric phase-transfer catalysts using hydrofluoric acid and application

2019 Fiscal Year Final Research Report

• Project/Area Number: 17K14451
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: University of the Ryukyus
• Principal Investigator: Arimitsu Satoru 琉球大学, 理学部, 助教 (30546982)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: フッ素 / 有機触媒 / 不斉反応

Outline of Final Research Achievements

First, the synthetic route for the our designed urea catalysts was established as expected. However, it was revealed expanding the substrate scopes is very difficult with this methodology. Therefore, other types of catalysts bearing strong hydrogen bonding acceptor groups were searched, and we found N-oxide is promising candidate. The many types of chinchona-based N-oxide catalysts were prepared, and we analyzed its potential of association with HF by 19F NMR, and it revealed that chinchona-based N-oxide catalysts actually has the ability to associate with HF. Next, the substrate effects of catalysts are now examined and will be applied for the asymmetric fluorination.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

本研究により、当初提案していたウレア触媒の合成を達成したものの、基質適応範囲の拡張が困難であることがわかった。しかし、同様のHF捕捉機能を持つNオキシドに着目し、シンコナルカロイド由来のNオキシド化合物の合成を達成し、実際にHFと会合することがわかった。本研究成果はHF水溶液を触媒反応に応用できる可能性を秘めており、今後引き続き触媒のデザインと反応開発を研究していく。