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アリル塩化物と原発アルキル塩化物のニッケル触媒型クロス電極結合
Seoyoung Kim1, Matthew J Goldfogel1, Michael M Gilbert1
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Journal of the American Chemical Society
|May 16, 2020
まとめ
この研究は,アリル塩化物とアルキル塩化物のクロス電極結合の最初の一般的な方法を示している. イオジドまたはブロミド添加物による新しいピリジン-2,6-ビス (N-シアノカルボキシミジン) リガンドは,この困難な変換を可能にします.
科学分野:
- 有機化学
- カタリシス
- 合成方法論
背景:
- アルキル塩化物とアリル塩化物は安定した炭素電ophilesですが,それらのクロスカップリングは困難です.
- 炭素核フィール結合の既存の方法は確立されていますが,アリルとアルキル塩化物のクロス電気フィール結合は有機合成における重要な課題です.
研究 の 目的:
- アリル塩化物とアルキル塩化物の交叉電極結合のための最初の一般的なアプローチを開発する.
- これらの電化基質に関連する固有の安定性の課題を克服するために.
主な方法:
- 最近開発されたリガンドであるピリジン-2,6-ビス (N-シアノカルボキシミジン) (PyBCamCN) を利用した.
- 少量のヨウ素またはブロミド添加物を含む触媒システムを使用しています.
- 反応の範囲と効率を35の異なる例で調査した.
主要な成果:
- アリル塩化物とアルキル塩化物のクロス電極結合の最初の一般的な方法を達成した.
- 反応の範囲を広く示し,平均63%±16%の産出率を示した.
- より反応性のあるアルキルハリドの低安定状態濃度を維持する重要なコカタライストとしてヨウ素およびブロミド添加物を特定した.
結論:
- 開発された方法は,クロス電離結合反応の重要な進歩を提供します.
- PyBCamCNリガンドとハリド添加物の使用は,挑戦的な基板組み合わせのための生産的で選択的な経路を提供します.
- この研究は 豊富で安定した原材料を用いて 複雑な分子を合成するための 新たな道を開きます
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