遷移金属によるフッ素脱離過程を利用したアリル位およびビニル位炭素-フッ素結合活性化

書誌事項

タイトル別名
  • Allylic and Vinylic Carbon-Fluorine Bond Activation via Transition Metal-Mediated and -Catalyzed Fluorine Elimination
公開日
2024-02-01
資源種別
journal article
DOI
  • 10.5059/yukigoseikyokaishi.82.130
公開者
公益社団法人 有機合成化学協会

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説明

<p>Since the carbon-fluorine (C-F) bond exhibits a high bond dissociation energy, chemical transformation involving its cleavage (C-F bond activation) has been difficult and a challenge in synthetic organic chemistry. As one solution to this problem, we established a new and efficient methodology for C-F bond activation under mild reaction conditions by taking full advantage of transition metal-mediated β- and α-fluorine elimination processes. In these studies, we investigated organometallic elementary steps such as (i) oxidative cyclization, (ii) nucleophilic addition, and (iii) electrophilic addition, as bond-forming processes that produce intermediates suitable for fluorine elimination. By combining these processes with fluorine elimination, we systematically developed various synthetic reactions via allylic and vinylic C-F bond activation of fluoroalkenes. In addition, fluorophilic boron or silicon compounds were found to serve as fluorine captors, thereby promoting catalytic reactions by regenerating active species from inert metal fluorides, which were often generated in metal-mediated fluorine elimination.</p>

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