モノフッ素アルケンの生成のためのジェム-二フッ素メチル群の選択的モノフッ素化とウィティグ機能化
Dipendu Mandal1, Richa Gupta1, Rowan D Young1
1Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Singapore.
Journal of the American Chemical Society
|August 19, 2018
まとめ
この研究は,ジェム-ディフローロメチル群の選択的モノデフローリネーションのための新しい挫折したルイスペア (FLP) 方法を導入しています. この方法では,二酸化メチル化合物を,利用可能な試薬を用いて有価なモノフッ素アルケーンに効率的に変換します.
科学分野:
- 有機化学
- 有機金属化学
背景:
- ジェム・ディフローロメチル群は重要な合成構成要素である.
- これらのグループの選択的な機能化は,合成的な課題であり続ける.
研究 の 目的:
- ジェム・ディフローロメチル群の選択的モノデフローリネーションのための新しい方法の開発.
- この変換における挫折ルイス対 (FLP) の有用性を探求する.
- 合成した活性化中間産物からモノフッ素アルケンを合成する.
主な方法:
- FLPの成分として様々なトリアリルフォスフィンとグループ13のルイス酸を調査した.
- 最適なFLP反応剤としてP{\o-Tol}3とB{\C6F}5を特定した.
- PPh3とBF3·OEt2のようなより経済的な反応剤で反応の実現性を示した.
- 活性化された中間物質のウィティグ反応プロトコルを使用した.
主要な成果:
- FLPのアプローチを用いて,ジェム-ディフローロメチル群の選択的モノデフローリネーションを達成した.
- 生成されたα-fluoroalkylphosphonium中間体は,選択性を確保するために,さらなるフッ素抽出のための活性が低下したことを示した.
- 多種多様なモノフッ素アルケンを合成した.
結論:
- FLP媒介によるモノデフローリネーションは,有価なモノフッ素アルケンの選択的かつ効率的な経路を提供します.
- この方法は,専門的で経済的な反応剤システムに適応できます.
- この研究は,ジェム・ディフローロメチル化合物の合成有用性を拡大する.
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