Dearomatizing Conversion of Aromatic Compounds Based on Addition Reactions of Boron Reagents

2015 Fiscal Year Final Research Report

• Project/Area Number: 25620082
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: Ohmura Toshimichi 京都大学, 工学(系)研究科(研究院), 准教授 (00378803)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 合成化学 / 芳香族化合物 / 複素環状化合物 / ホウ素 / 付加反応

Outline of Final Research Achievements

Addition of a diboron reagent into aromatic compounds containing two nitrogen atoms, that is 4,4’-bipyridines, took place efficiently at 60-110 °C under transition-metal-free conditions to give dearomatized compounds in good yields. The boryl group on the dearomatized compounds might be transferred to unsaturated organic molecules, such as pyrazines and alkynes, under mild conditions (room temperature ~ 60 °C). Based on these two elementary reactions, 4,4’-bipyridine-catalyzed diboration of pyrazines and alkynes was established. The insights obtained by this research would be useful for development of molecular transformations based on dearomatization.

Free Research Field

有機金属化学、有機合成化学