Strategy development for rapid increase in complexity and diversity of phosphorus-containing polyaromatic compounds

2014 Fiscal Year Final Research Report

• Project/Area Number: 26620086
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: TOBISU Mamoru 大阪大学, 工学(系)研究科(研究院), 准教授 (60403143)
• Project Period (FY): 2014-04-01 – 2015-03-31
• Keywords: 均一系触媒反応 / π共役化合物 / クロスカップリング / リン化合物

Outline of Final Research Achievements

To establish robust synthetic strategy to rapidly increase both complexity and diversity of pai-conjugated compounds, the following investigation has been performed. 1) Catalytic construction of pai-conjugated scaffold: Compared to phosphorus-linked biaryl compounds (i.e., phosphole), the corresponding six-membered phophacycles (phosphorus-bridged biaryl ether or amine) are less explored, especially in terms of their catalytic synthesis. Our newly developed cyclization method via C-P bond cleavage has successfully been applied to the synthesis of polyannulated six-membered phosphacycles. 2) Late stage functionalization of pai-conjugated molecules via C-O bond cleavage: In this study, a robust methoxy group is demonstrated to serve as a versatile handle for the introduction of an alkynyl group to siloles, ferrocenes and polyaromatics at the late stage of synthesis by using a nickel-based catalyst. The flexible synthesis of dibenzochrysene was also accomplished.

Free Research Field

有機合成化学