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Updated: Jun 16, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

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モノフローロベンゼンにおけるC-F活性化のための二酸化アルシントンまたは単体アルシントンとしてのダイアルメン

Xufang Liu1, Shicheng Dong2, Jun Zhu3

  • 1TUM School of Natural Sciences, Department of Chemistry, Institute of Silicon Chemistry and Catalysis Research Center, Technische Universität München, Lichtenbergstraße 4, Garching bei München 85748, Germany.

Journal of the American Chemical Society
|August 21, 2024
PubMed
まとめ

この研究は,中性ダイアルメンを用いて強い炭素-フッ素 (C-F) 結合を活性化するための新しいアルミニウム媒介法を導入しています. この突破により 以前は難しいと考えられていた 有機金属化合物の新合成経路が 可能になりました

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Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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