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リモートメタ-C-Hボンドのクロスカップリングは,U形のテンプレートによって指示されます

Li Wan¹, Navid Dastbaravardeh, Gang Li

¹Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|November 19, 2013

まとめ

研究者は,除去可能なニトリルテンプレートを使用して,3-フェニルプロパノ酸およびフェノール誘導体のメタ-C-Hアリレーションおよびメチレーションを開発しました. この方法により,有機ボロンと効率的なC−H結合のクロスカップリングが可能になります.

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

背景:

直接的なC-H機能化は,伝統的な方法と比較して,複雑な分子へのより原子経済的な経路を提供します.
選択的で効率的なC-H活性化戦略の開発は,合成化学における重要な課題です.

研究の目的:

3-フェニルプロパノ酸およびフェノール誘導体のメタ-C-Hアリレーションおよびメチレーションのための新しい方法を開発する.
C-H機能化の方向化における取り外し可能なニトリルテンプレートの役割を調査する.
パラジウム触媒によるクロスカップリング反応におけるU型テンプレートとアミノ酸リガンドの有用性を調査する.

主な方法:

メタ選択的なC-H機能化を達成するために,取り外し可能なニトリル誘導群を使用しました.
U型テンプレートと,パラジウム触媒におけるモノ保護アミノ酸リガンドの組み合わせを使用した.
様々なオルガノボロン反応剤とのC-H結合の交互結合を調査した.

主要な成果:

ターゲット基質のメタ-C-Hアリレーションとメチレーションを成功裏に達成しました.
地域選択性を指向するニトリルテンプレートの有効性を実証しました.
効率的なC−H結合のクロスカップリングのためのU型テンプレートとアミノ酸リガンドの相乗効果を特定しました.

結論:

メタ-C-H アリレーションとメチレーションのための新しい効率的な方法が確立されています.
リムーバブルニトリルテンプレート戦略は,C-H機能化のための汎用的なプラットフォームを提供します.
開発された触媒システムは,複雑な有機分子を構築するための強力なツールを提供します.

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