アミドC-N結合活性化によるNi-触媒アルケンの炭酸酸化
James A Walker1, Kevin L Vickerman1, Jenna N Humke1
1Department of Chemistry, Iowa State University , Ames, Iowa 50011, United States.
Journal of the American Chemical Society
|July 15, 2017
まとめ
この研究は,アリルボロン酸ピナコールエステルを用いて,オアリルベンザミドのカルボアシレーションのための新しいニッケル触媒反応を導入する. この方法は,アミドC-N結合を活性化することによって,2-ベンジル-2,3-二水素-1H-インデン-1-オンを効率的に合成します.
科学分野:
- 有機化学
- カタリシス
- 合成方法論
背景:
- アルケンのカルボアシレーションは貴重な合成変換である.
- 伝統的な方法はしばしばC-C結合の活性化に依存し,これは困難である.
- アミドC-N結合の活性化が代替的な経路を提供している.
研究 の 目的:
- オアリルベンザミドの新しいNi-触媒形式カルボアシレーションを開発する.
- アリルボロン酸ピナコールエステルを結合パートナーとして利用する.
- 2-ベンジル-2,3-ジヒドロ-1H-インデン-1-オンを合成するための新しい経路を確立する.
主な方法:
- ニッケル ((0) 触媒を用いてアミドC−N結合を活性化した.
- 反応のメカニズムは酸化添加,アルケンのNi (II) - アシル結合への挿入,および還元性除去を含む.
- 多様な代替オアリルベンザミドとアリルボロン酸ピナコールエステルは基板として使用された.
主要な成果:
- 反応はエクソ選択性で進み,2-ベンジル-2,3-二水素-1H-インデン-1-オンを生成した.
- 目標製品では中等から高い収穫率 (46-99%) が達成された.
- その範囲には様々なアリルボロン酸ピナコールエステルと代替オアリルベンザミドが含まれていた.
結論:
- アミドは,C-N結合活性化によるアルケンの炭酸酸化のための有効な基質である.
- このアプローチは,C-Cボンドの活性化戦略に実用的な代替手段を提供します.
- 開発された方法はインデノンの誘導体を合成するための新しいツールを提供します.
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