活性化されていないアルケンをフッ素イオンでカーボフッ素化

Zhonglin Liu¹, He Chen¹, Ying Lv²

¹Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , P. R. China.

Journal of the American Chemical Society

|April 26, 2018

まとめ

銅触媒は,フッ素イオンを使用してアルケンの根性カルボフッ素化を可能にします. この方法は,活性化されていないアルケンと様々なアルキル塩化物から炭素化製品を効率的に生成し,広範な適用性を示しています.

科学分野:

有機化学
カタリシス
化化学

背景:

活性化されていないアルケンのカーボフローリネーションは依然として困難です.
有機分子にフッ素を導入するための効率的で多用途な方法の開発は極めて重要です.

研究の目的:

活性化されていないアルケンのための銅アシストラジカルカルボフローリネーションプロトコルを開発する.
非活性化アルケンの銅触媒によるフッ素トリフッ素メチル化について調べる.

主な方法:

フッ素源として銅複合体 ([Cu(L3) F2]H2O) と,塩化物除去剤として銀複合体 ([Ag(DMPhen) ((MeCN) BF4) を利用した.
炭酸四塩化物 (CCl4) と他の活性化アルキル塩化物を基板として使用している.
セシウムフッ素 (CsF) とウメモトの反応剤を用いた銅触媒によるフッ素トリフルオロメチル化を開発した.

主要な成果:

活性化されていないアルケンのカルボフローリネーション製品で満足のいく結果が得られた.
幅広い機能群の互換性と広範囲の基板の適用が実証されている.
銅触媒によるフッ素トリフルオロメチル化反応が成功しました

結論:

開発された銅補助プロトコルは,活性化されていないアルケンの根性カルボフッ素化のための効率的な経路を提供します.
方法論は多用途で,様々なアルキル塩化物に適用できます.
Cu ((II) -F複合体からアルキル基へのフッ素原子移転を含むメカニズムが提案されています.

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