Regulation of transition states of catalytic reactions through the formation of halogen-bonding

2018 Fiscal Year Final Research Report

• Project/Area Number: 16KT0162
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 特設分野
• Research Field: Transition State Control
• Research Institution: Osaka University
• Principal Investigator: Takeda Youhei 大阪大学, 工学研究科, 准教授 (60608785)
• Project Period (FY): 2016-07-19 – 2019-03-31
• Keywords: ハロゲン結合 / イミダゾリウム塩 / 遷移状態 / 有機触媒 / 協働触媒 / 計算科学 / 官能基選択的

Outline of Final Research Achievements

This research was aimed at the development of new organocatalytic reactions through the formation of halogen-bonding as the key driving force in the recognition and activation of substrates, based on theoretical and experimental methods. A new halogen bonding donor with the polyfluorinated core, which is expected to exhibit stronger Lewis acidity than previously known imidazolium sails-based halogen bonding donors, was successfully developed. Furthermore, the evaluation of the structural factors on the properties as halogen donors by DFT was conducted. The utilization of the halogen donors as a soft Lewis acid in organocatalytic reactions was attempted.

Free Research Field

有機合成化学、触媒化学、有機機能材料化学

Academic Significance and Societal Importance of the Research Achievements

希薄溶液中におけるハロゲン結合は水素結合よりも弱いために、触媒分野において基質活性化のための相互作用としては長い間見過ごされてきた。本研究で得られた成果であるハロゲン結合ドナーの構造と反応性に関する相関関係は、未解明であったハロゲン結合の遷移状態に関する情報を解明することにより、新たな有機触媒設計を可能にする点で、ものづくりにおいて欠かせない触媒化学の新展開を切り拓くことができ、学術界のみならず産業界にも大きな波及効果がある。