フェノルをアロマティックアミンに変換するためのアリルカルバマートのニッケル触媒分解

Akihiro Nishizawa¹, Tsuyoshi Takahira¹, Kosuke Yasui¹

¹Department of Applied Chemistry, Graduate School of Engineering , Osaka University , Suita , Osaka 565-0871 , Japan.

Journal of the American Chemical Society

|April 25, 2019

まとめ

この研究は,フェノルを芳香性アミンに変換する新しいニッケル触媒反応を導入します. この方法は,従来の方法とは異なり,副産物として二酸化炭素のみを生成することで,廃棄物を最小限にします.

科学分野:

有機化学
カタリシス
持続可能な化学

背景:

フェノルをアロマティックアミンに変換する伝統的な方法は,多くの場合,重要な廃棄物を発生させる活性化グループを必要とします.
現存するフェノールの触媒性アミネーションは,機能群互換性によって制限される.

研究の目的:

フェノールからアロマティックアミンを合成するためのより持続可能で効率的な触媒方法を開発する.
現在の合成経路における廃棄物生成と機能グループ不適合の制限を克服する.

主な方法:

アリルカルバメートの新しいニッケル触媒デカルボキシル化が採用された.
ポリスチレン基板 (PS-DPPBz) に固定されたキービスフォシンリガンドを使用した.
機能群の耐性を高めるために,自由アミンが存在しない状態で反応を行った.

主要な成果:

唯一副産物として二酸化炭素を用いたフェノールから芳香性アミンが成功して合成された.
固定された触媒 (PS-DPPBz) は,サポートされていない変種と比較して,著しく高い活性を示した.
この反応は,ホルミール群の耐性を含め,幅広い機能群相容性を示した.

結論:

この新しい触媒的アプローチは芳香性アミンへのよりグリーンで効率的な経路を提供します
イモビライズされたリガンドの使用は,触媒の活性を強化し,潜在的な触媒の回復を簡素化します.
このメソッドの機能群の許容性は,有機合成におけるその適用性を拡大する.

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