イリジウム触媒によるボリル化によるアレンのシアネーション
Carl W Liskey1, Xuebin Liao, John F Hartwig
1Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801-3602, USA.
Journal of the American Chemical Society
|August 4, 2010
まとめ
この研究は,イリジウム触媒C-Hボリレーションと銅媒介シアネーションを使用して,アレンのメタシアネーションのためのワンポット方法を導入しています. この効率的なプロセスは,多様な芳香化合物からメタ置換されたアリルニトリルを合成します.
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:
- アリルニトリルは,医薬品と材料科学における重要な構成要素である.
- アレナのメタポジションに機能化を向けることは,合成的な課題であり続けています.
- メタシアネーションの既存の方法は,多くの場合,多段階の手順または厳しい条件を必要とします.
研究 の 目的:
- アレンのメタシアン化のための新しいワンポット方法の開発.
- アリルボロナートエステルおよび酸の銅媒介シアネーションのための効率的な条件を確立する.
- メタ置換アリルニトリル合成のための開発された方法論の広範な適用性を実証する.
主な方法:
- アレンの1ポテンツ連続イリジウム触媒C-Hボリレーション.
- in-situで生成されたアリルボロナートエステルの銅媒介シアネーション.
- ボリレーションとシアネーションの2段階の反応条件の最適化.
主要な成果:
- 様々なアレンやヘテロアレンからメタ置換されたアリルニトリルの合成が成功しました.
- ハリド,ケトン,エステル,アミド,保護アルコールを含む多様な機能群との互換性が実証されています.
- 保護されたフェノルをエトラウィリン合成の重要な中間物質に効率的に変換する.
- メタ置換されたベンゾニトリルのアルデヒド,ケトン,アミド,カルボキシル酸,テトラゾール,ベンジラミンへのさらなる誘導.
結論:
- 開発されたワンポット・メソッドは,メタ置換されたアリルニトリルへの効率的で汎用的な経路を提供します.
- この方法論は,潜在的医薬品用途を持つ複雑な芳香化合物の合成を簡素化します.
- 報告された条件は,C-H機能化とシアネーション反応の範囲を拡大します.
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