ベンジル塩化物と単純なオレフィンによるニッケル触媒ヘック型反応
Ryosuke Matsubara1, Alicia C Gutierrez, Timothy F Jamison
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Journal of the American Chemical Society
|November 10, 2011
まとめ
この研究は,非活性化アルケンのベンジル化のための新しいニッケル触媒法を導入しています. このプロセスは,室温で1,1-非置換オレフィンに対する高い選択性を持つ機能化されたアルリルベンゼン誘導体を効率的に生成します.
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:
- アリルベンゼン誘導体は,価値ある合成中間物質である.
- アルケンの機能化のための既存の方法は,しばしば活性化基板または厳しい条件を必要とします.
- パラジウムで触媒化された変種は,典型的には1,2-非置換オレフィンを生成する.
研究 の 目的:
- 活性化されていないアルケンのニッケル触媒による新しい分子間ベンジル化を開発する.
- 1,1-非置換アルリルベンゼン誘導体の高い選択性を達成するために.
- 穏やかで汎用的な合成経路を確立するために.
主な方法:
- ニッケル触媒によるクロスカップリング反応.
- ベンジル塩化物と,エチレンを含む非活性化アリファティックオレフィンを使用する.
- 室温の反応条件.
主要な成果:
- 機能化されたアルリルベンゼン誘導体の合成に成功した.
- ベンジル塩化物とアルケンのカップリングパートナーの両方に広範な基板の範囲.
- 1,1-非置換オレフィンに対する高い選択性があり,パラジウム触媒法とは対照的です.
- 電子的に偏らないアリファティックオレフィンとの効率的な反応.
結論:
- ニッケル触媒は,アルケンのベンジル化のための新しい経路を提供します.
- 開発された方法は,1,1-非置換アルリルベンゼンへの穏やかで選択的な経路を提供します.
- このアプローチは,クロスカップリング反応における活性化されていないアルケンの有用性を拡大します.
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