Development of dearomative reaction controlled by directing leaving group

2018 Fiscal Year Final Research Report

• Project/Area Number: 17K14453
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Waseda University
• Principal Investigator: MUTO Kei 早稲田大学, 理工学術院, 講師(任期付) (60778166)
• Research Collaborator: Komatsuda Masaaki ; Kayashima Yuki ; Yanagimoto Aika ; Yamaguchi Junichiro
• Project Period (FY): 2017-04-01 – 2019-03-31
• Keywords: 脱芳香族化 / 脂環式化合物 / ベンジルアルコール / 結合切断 / アリル化

Outline of Final Research Achievements

We developed a Pd-catalyzed dearomative allylation of benzylphosphates as well as carbonates. Of note, this reaction can proceed by using aromatic substrates as a limiting reagent in a catalytic manner. The use of electron-rich triarylphosphine as a ligand accelerates reaction. We succeeded in the derivatization of dearomative products to synthesize valuable acyclic building block.
Moreover, based upon this work, we also discovered dearomative allylations of other benzyl substrates.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

芳香族化合物は無尽蔵に存在する、最も普遍的な構造体である。それらを脱芳香族的に官能基化し、三次元構造をもつ脂環式化合物を合成することができれば、これまで合成に多段階を要する、もしくは合成し得なかった分子群をてにすることができる。特に三次元構造をもつ化合物は医農薬において特異な生物活性を示すため、本研究の進展は有機合成分野のみならず創薬化学などへの波及効果も期待できる。