ポリフッ素アルケンの銅触媒による地域選択的モノデフッ素ボリレーションによる様々なフッ素アルケンの生成
Hironobu Sakaguchi1, Yuta Uetake2, Masato Ohashi1
1Department of Applied Chemistry, Faculty of Engineering, Osaka University , 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan.
Journal of the American Chemical Society
|August 30, 2017
まとめ
ポリフッ素アルケンの銅触媒モノデフッ素ボリレーションは,価値あるフッ素アルケンの誘導体を合成するための多用途な方法を提供します. この反応は基板の範囲が広く,合成の実用性が向上し,薬物模倣のような複雑な分子の生成を可能にします.
科学分野:
- 有機化学
- キャタリシス
- フッ素化学
背景:
- ポリフッ素アルケンは有機合成における重要な構成要素である.
- 効率的な機能化方法を開発することが不可欠です.
- モノデフローロボリレーションは,ボールの機能群を選択的に導入するための経路を提供します.
研究 の 目的:
- ポリフッ素アルケンの地域選択的銅触媒モノデフッ素ボリレーションを開発する.
- この新しい合成方法の範囲と限界を探求する.
- 結果として得られるフッ素アルケニルボロン化合物の有用性を,さらなる変換で実証する.
主な方法:
- 様々なポリフルオアルケンの銅触媒反応とディボロン反応剤.
- 触媒,溶媒,温度を含む反応条件の最適化
- ビスコラト・ディボロンやビスコラト・ネオペンチル・グリコラト・ディボロンなどの異なるボロン源の調査.
- 安定性と隔離性を高めるため,トリフローロボラート塩に製品の誘導化.
主要な成果:
- 多種多様なポリフッ素アルケンの地域選択性モノデフッ素ボリレーションを達成し, (二酸化フッ素) アレン,テトラフッ素エチレン, (三酸化フッ素) アレン,およびトリフッ素メチル化されたモノフッ素アルケンを含む.
- [Bpin]2と (Bnep) 2の最適ボロン源は, (二酸化リウ素) アレンのアリル基の電子特性により特定された.
- 安定した三酸塩の分離により,合成の実用性が向上したことが示された.
- 地域選択性は,基質に依存するβ-フッ素除去方式によって支配されていることが示された.
結論:
- 開発された銅触媒によるモノデフローロボリレーションは,温和で地域選択的で広く適用可能な方法である.
- トリフローロボラート塩の容易な分離は,反応の合成有用性を高める.
- 合成されたフッ素アルケニルボロン化合物は,潜在的製薬剤を含む有価な派生剤に容易に変換できます.
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