二次性アシクロアミドのPd触媒によるN-アリレーション:触媒の開発,範囲,計算研究

Jacqueline D Hicks¹, Alan M Hyde, Alberto Martinez Cuezva

¹Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.

Journal of the American Chemical Society

|November 6, 2009

まとめ

この研究では,アリルハリドを使用したアミドの効率的なN-アリレーション法が導入されています. 新しいビアリルフォスフィンリガンドにより,多様な三次アリルアミドの簡単な合成が可能になる.

科学分野:

有機化学オーガニック・ケミストリー
カタリシスカタリシスカタリシス
合成方法論合成方法論

背景:

三次アリルアミドは,医薬品や材料における重要な構造モチーフである.
アミドのN-アリレーションの効率的な方法は,合成の柔軟性にとって極めて重要です.

研究の目的:

アサイクリック二次アミドの効率的なN-アリレーションプロトコルを開発する.
三次アリルアミドの芳香成分を容易に変化させるため.
この変換のための新しいフォスフィンリガンドの重要な特徴を特定し,理解する.

主な方法:

アリルノナフラート,トリフラート,塩化物を用いたアミドのN-アリレーション.
新しいビアリルフォスフィンリガンドの開発と応用.
リガンド効果を調査するための合成,機械,および計算研究.

主要な成果:

アサイクリック二次アミドの効率的なN-アリレーションが達成された.
3,5-(bis) トリフルオロメチルフェニル群を持つ新しいビアリルフォスフィンリガンドは,ユニークな有効性を実証しました.
リガンドの最適化により,メトキシ群と電子取り除く置換物質が活性化に不可欠であると特定されました.

結論:

三次アリルアミドを合成するための堅牢で多用途な方法が確立されています.
開発されたビアリルフォスフィンリガンドは,その特殊な電子およびステリック特性により,非常に有効です.
計算データは,アミド結合を促進する電子欠乏リガンドを含む提案されたメカニズムを支持しています.

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