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エンドオセレクティブ Pd-触媒化されたシリルメチルヘック反応
Marvin Parasram1, Viktor O Iaroshenko, Vladimir Gevorgyan
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
Journal of the American Chemical Society
|December 16, 2014
まとめ
シリルエーテルを用いた新しいパラジウム触媒ヘック反応により,周期性化合物の合成が可能になる. このシリコン補助プロセスは,高いエンド選択性を達成し,貴重な (Z) -アルケニルダイオルを産出します.
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
- 合成方法論 合成方法論
背景:
- ヘック反応は,炭素-炭素結合形成のための強力なツールです.
- ヘック反応において高いステレオ選択性を達成することは,依然として課題です.
- シリコンを含む反応剤は,ユニークな反応性および選択性プロファイルを提供します.
研究 の 目的:
- 周期性化合物の合成のための新しいパラジウム触媒ヘック反応を開発する.
- この新しい反応のメカニズムとステレオ化学的結果を調査する.
- 合成された製品の有用性を探求する.
主な方法:
- フェノールとアリファティックアルケノールのイオドメチルシリルエーテルを用いたパラジウム触媒ヘック反応.
- ハイブリッドのパラジウム-ラジカル経路を含むメカニズム研究.
- アリル性シリロキシサイクルを (Z) -アルケニルジオールに酸化する.
主要な成果:
- エンドオセレクティブヘック反応の発達.
- ハイブリッドのパラジアム-ラジカルメカニズムを特定する.
- エンドオセレクティブ性の達成におけるシリコンの重要な役割の実証.
- 反応産物から (Z) -アルケニルダイオルの合成が成功しました.
結論:
- 新しく効率的なシリルメチルヘック反応が確立されました.
- この反応は,ユニークなハイブリッドのパラジアム・ラジカルメカニズムによって進行する.
- シリコンは,エンド選択性を制御する上で重要な役割を果たします.
- 開発された方法論は,貴重な (Z) -アルケニル二酸化物へのアクセスを提供します.
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