インドルの銅触媒によるN-アリレーション
Jon C Antilla1, Artis Klapars, Stephen L Buchwald
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Journal of the American Chemical Society
|September 26, 2002
まとめ
新しい触媒法により,N-アリリンドールを効率的に合成する. この銅で触媒化された結合反応は,容易に入手可能な出発材料を使用し,インドール機能化のための高収量経路を提供します.
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:
- インドール誘導体は,医薬品化学と材料科学における重要な支架である.
- インドールのN-アリレーションの効率的な方法は,複雑な分子を合成するために非常に求められています.
研究 の 目的:
- インドルのN-アリレーションのための一般的で効率的な触媒方法を開発する.
- この変換のためのダイアミンリガンドを持つ銅 (I) ヨウ化物 (CuI) ベースの触媒の有用性を調査する.
主な方法:
- カタリストの前駆体として,銅 (I) ヨウ化物 (CuI) を利用した.
- トランス-1,2-サイクロヘキサンジアミン (1a),トランス-N,N'-ジメチル-1,2-サイクロヘキサンジアミン (2a),およびN,N'-ジメチル-エチレンジアミン (3) を含む様々なダイアミンリガンドが使用されています.
- アリルイオジドまたはアリルブロミドを様々なインドルと結合させることを研究した.
主要な成果:
- N-アリリンドール製品の高収量を達成しました.
- 様々なインドールとアリルハリドの方法の汎用性を示した.
- N-arylationを触媒化するために特定のダイアミンリガンドとCuIを成功裏に使用しました.
結論:
- 報告された方法は,N-アリリンドールへの堅牢で高収量な経路を提供します.
- この触媒システムは,機能化されたインドールの合成のための貴重なツールを提供します.
- 簡単に入手可能な銅触媒とダイアミンリガンドの使用により,この方法は合成化学者にとって実用的です.
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