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アリルパラジウム触媒と阻害モノデント酸アニリドを用いたアミドα,β脱水

Yifeng Chen¹, Aneta Turlik¹, Timothy R Newhouse¹

¹Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Journal of the American Chemical Society

|January 22, 2016

まとめ

新しい方法は,パラジウム触媒と新しいリチウムN-サイクロヘキシルアニリド反応剤を使用して,アミドの直接のα,β脱水化を可能にします. このアプローチは,広範囲の基板を持つ有価な化学的中間物質を合成するための実用的な経路を提供します.

科学分野:

有機化学
カタリシス
合成方法論

背景:

アミドの機能化は有機合成において極めて重要です.
アミドの直接的なα,β脱水化は,合成上の課題である.
パラジウム触媒反応は,C-H機能化のための強力なツールを提供します.

研究の目的:

アミドのα,β脱水化のための実用的で直接的な方法を開発する.
新しいリチウムN-サイクロヘキシルアニリド (LiCyan) 反応剤のパラジウム触媒の有用性を調査する.

主な方法:

脱水反応のためにアルリルパラジウム触媒を用いた.
新しいリチウムN-サイクロヘキシルアニリド (LiCyan) を主要反応剤として合成し,使用した.
最適な基板範囲と効率のための反応条件を調査した.

主要な成果:

様々なアミドの直接のα,β脱水化が成功しました.
触媒サイクルを容易にするために,リシアン反応剤の重要な役割を実証した.
酸性ヘテロアトム核愛素を含む幅広い機能群に対する耐性を示した.

結論:

アミドα,β-脱水化のための新しく効率的なパラジウム触媒法が確立されています.
開発されたプロトコルは,直接的で実用的な合成経路を提供します.
LiCyan反応剤は,この変換の成功の鍵であり,広範囲の基板適用を可能にします.

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