Design and development of hydrogen bond donor/phosphonium salt bifunctional catalysts

2019 Fiscal Year Final Research Report

• Project/Area Number: 17K14483
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Shinshu University
• Principal Investigator: Toda Yasunori 信州大学, 学術研究院工学系, 助教 (60758978)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: 有機分子触媒

Outline of Final Research Achievements

First, the mechanism of bifunctional tetraarylphosphonium salts-catalyzed [3+2] reactions of epoxides and carbon dioxide was investigated, revealing the substituent effect of the phosphonium salt catalysts. It was also found that the [3+2] reactions proceeded efficiently by a combined use of phosphonium ylides and metal salts as a catalyst. Next, the [3+2] reactions of epoxides with isocyanates were performed in the presence of a tetraarylphosphonium salt catalyst, where the corresponding oxazolidinones were obtained in good yields. In contrast, switched regioselectivity was observed in the case of glycidol, affording 4-hydroxymethyl oxazolidinones.

Free Research Field

合成化学

Academic Significance and Societal Importance of the Research Achievements

環境調和型物質合成プロセス開発の観点から、分子変換における効率の向上と選択性の獲得が求められており、化学反応を精密に制御し、高度な分子変換を実現する新規触媒の開発は重要な研究課題である。本研究では、反応を精密制御できる高活性な有機分子触媒として、新規テトラアリールホスホニウム塩触媒を開発し、これを用いる多様な分子変換技術の開発を行った。研究期間内に検討した反応は、工業的にあるいは医薬品合成などにおいて重要な生成物を与え、新規触媒の開発という学術的な観点だけでなく社会における合成化学的な観点からも大変意義深い。