Development of catalytic dearomative functionalization of arenes by ligand-controlling reaction space of catalysts

2020 Fiscal Year Final Research Report

• Project/Area Number: 19K15573
• 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: Waseda University
• Principal Investigator: MUTO Kei 早稲田大学, 高等研究所, 講師(任期付) (60778166)
• Project Period (FY): 2019-04-01 – 2021-03-31
• Keywords: 脱芳香族化 / 脂環式化合物 / パラジウム触媒 / 多成分反応 / 芳香族分子

Outline of Final Research Achievements

In this study, it was succeeded to develop dearomative functionalizations to realize the novel synthetic method of alicyclic molecules from planer aromatic molecules. Among various aromatic molecules, this study focused on benzenoids those are the most abundant but difficult to be transformed.
In this study, we succeeded to develop dearomative C-C bond formation of aromatic cyanohydrins as well as bromoarenes. These reaction proceeds even when only one equivalent of arenes were used. Moreover, we showcased the synthetic utility of these methods by elaborating products to highly three-dimensional alicyclic molecules.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

三次元性の高い脂環式分子群は高い生物活性や標的タンパク質選択性を示すため、近年創薬化学において再注目される構造単位である。本研究では、石油資源や医薬品候補化合物群のどちらにも多く見られるユビキタスな分子構造単位である芳香族分子を三次元性の高い分子へ迅速な変換を可能にする新規手法の開発を目指した。本研究の成熟は、複雑三次元構造分子の短工程合成や、迅速な医薬品候補分子探索の助けとなり、有機合成化学の枠を超えて波及効果を及ぶすことができる。
また、短工程合成は廃棄物の少ない分子合成に直結するため、SDGsの要求も満たす。