Synthesis of conjugated organic compounds using fluorinated isobenzofurans

2019 Fiscal Year Final Research Report

• Project/Area Number: 16H04143
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Gunma University
• Principal Investigator: Amii Hideki 群馬大学, 大学院理工学府, 教授 (00284084)
• Co-Investigator(Kenkyū-buntansha): 杉石 露佳 群馬大学, 大学院理工学府, 助教 (30636220)
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: フッ素 / 有機合成化学 / トリフルオロメチル基 / イソベンゾフラン / 環化付加 / 共役化合物

Outline of Final Research Achievements

Fluorinated isobenzofurans are considered to be promising building blocks for the synthesis of fluorine-containing carbocyclic and heterocyclic systems. We have developed a novel method for the generation of trifluoromethylated isobenzofurans. The cascade trifluoromethylation/intramolecular acetalization of o-phthalaldehyde proceeded smoothly to give the lactol in high yield. The lactol easily underwent dehydration under acidic conditions to generate trifluoromethylated isobenzofuran, which underwent the intermolecular Diels-Alder reactions with alkenes to give the adducts in good yields. The resultant bicyclo compounds are good precursors of functionalized 1-trifluoromethylnaphthalenes. For instance, [4+2] cycloaddition with naphthpquinone and the subsequent transformations gave trifluoromethylated tetracene. We have obtained several interesting products by the [4+2] cycloaddition of trifluoromethylated isobenzofuran with 1,4-benzoquinone and acenaphthylene.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

π共役系有機化合物は、光電子物性を司る主幹構成部位として、材料、デバイス開発の根幹を担っている。共役系が拡張した化合物は、一般的には空気中で不安定なものが多い。今回の一連の研究により、フッ素の特性を活かして、多様な構造をもつ安定なπ共役系有機分子を選択的に合成する方法を見出だした。本研究が新しい材料創製に繋がることを期待している。