The development of bismuth-catalyzed dehydrogenative cross coupling and its application

2023 Fiscal Year Final Research Report

• Project/Area Number: 22K20709
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Multi-year Fund
• Review Section: 0801:Pharmaceutical sciences and related fields
• Research Institution: University of Toyama
• Principal Investigator: Kasama Kengo 富山大学, 学術研究部薬学・和漢系, 助教 (40963236)
• Project Period (FY): 2022-08-31 – 2024-03-31
• Keywords: ビスマス / ビアリール / クロスカップリング / 酸化反応 / 脱水素型カップリング

Outline of Final Research Achievements

Bismuth (Bi), a typical metal, is known as a safe and inexpensive element that can replace highly toxic transition metals. The development of Bi-catalyzed reactions has recently attracted attention. Since Bi has little known function as a redox catalyst, in this study, we have developed the dehydrogenative cross-coupling (CDC) reactions using Bi as a catalyst. As a result, the CDC reaction of 3-hydroxycarbazole and 2-naphthol was successfully developed under bismuth triflate-oxygen conditions. The reaction was found to be applicable to a wide variety of substrates, and 21 desired coupling products were obtained in up to 94% yield.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究は、これまで酸化還元機能はほとんど知られていない典型金属ビスマスを酸化還元触媒として利用できることを示し、ビスマス化学の発展に貢献した。さらに、今回開発したビスマス触媒反応は、入手容易なBiを用いて、安全で効率よくビアリール化合物ライブラリを拡充できることから、新たなケミカルスペースを提供することで創薬化学の発展への貢献が期待される。