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2014 Fiscal Year Final Research Report

Challenge to Enantioselective C-F Bond Activation

Research Project

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Project/Area Number 24655073
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionGunma University

Principal Investigator

AMII Hideki  群馬大学, 大学院理工学府, 教授 (00284084)

Project Period (FY) 2012-04-01 – 2015-03-31
Keywords有機合成化学 / フッ素 / 不活性結合 / 不斉反応 / 脱フッ素化 / クロスカップリング / 選択的変換
Outline of Final Research Achievements

Organofluorine compounds are widely used as materials such as polymer, liquid crystals, pharmaceutical and agrochemical compounds, and so on. Meanwhile, a new technology for highly selective synthesis of enantiomerically pure organofluorine compounds has been required. Toward stereoselective C-F bond activation, we examined Lewis acid-mediated defluorinative alkylation using gem-difluoromethylene compounds. Organoaluminum compounds were found to promote C-F bond activation of β-fluoro ethanol derivativess. When β, β-difluoro ethanols were treated with a stoichiometric amount of trimethylaluminum, defluorination and the subsequent methylation proceeded smoothly to give the ketones in moderate yields. For the preparation of several gem-difluoromethylene substrates, we developed the cross-coupling routes to 2-aryl-2,2-difluoroacetates. Furthermore, a new strategy for the synthesis of monofluoro compounds involving Mg-promoted defluorination of 2-aryldifluoroacetates have been invented.

Free Research Field

有機合成化学

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Published: 2016-06-03  

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