Development of Photoinduced Functionalization via Cleavage of Unreactive Aromatic C-N Bond

2023 Fiscal Year Final Research Report

• Project/Area Number: 22K14684
• 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: Kyushu University
• Principal Investigator: Sekine Kohei 九州大学, 先導物質化学研究所, 助教 (30843148)
• Project Period (FY): 2022-04-01 – 2024-03-31
• Keywords: 芳香族アミン / アルケン / ボリル化 / 二官能基化 / 炭素－窒素結合切断 / 有機光反応

Outline of Final Research Achievements

The transformations of aromatic amines via C-N bond cleavage were investigated. The divergent deaminative borylation and hydrodeamination of primary aromatic amines were developed. These transformations can be switched by the reaction conditions. Furthermore, based on the plausible reaction mechanism of the borylation, we have developed the difunctionalization of alkenes using aromatic amine derivatives as bifunctional reagents. The research provided the possibility of the development of the C-C bond forming reactions via C-N bond cleavage.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

工業的に生産され、豊富に存在する芳香族アミン類を原料とした有機反応の合成的利用価値は高い。本研究では、これまで高難度であり変換手法が限定的であった芳香族炭素－窒素結合の切断を伴う反応の開発し、芳香族アミン類を資源とする新しい分子変換技術の創出への可能性を示した。