Controlled Synthesis of α-CF2H or α-CF2Cl Styrenes from the Same Precursors: Dehydrazinative Hydrogenation or Chlorination of 3,3-Difluoroallyl Hydrazines,The Journal of Organic Chemistry

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Controlled Synthesis of α-CF2H or α-CF2Cl Styrenes from the Same Precursors: Dehydrazinative Hydrogenation or Chlorination of 3,3-Difluoroallyl Hydrazines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.joc.3c00355
Qinshuang Su ₁ , Haotian Gao ₁ , Guiping Qin ₁ , Yubo Jiang ₁ , Tiebo Xiao ₁

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By carefully choosing the reaction conditions, we have developed the controllable FeCl₃- or CuCl₂-mediated dehydrazinative hydrogenation or chlorination of 3,3-difluoroallyl hydrazines to access α-CF₂H or α-CF₂Cl styrenes. The current reaction provides for the first time a facile method for the direct and selective synthesis of α-CF₂H and α-CF₂Cl styrenes starting from the same precursors, which is easy to scale up and displays a broad substrate scope and good functional group tolerance. Moreover, product derivatization experiments demonstrated that the resulting α-CF₂Cl styrenes are practical and versatile building blocks for the diversified synthesis of fluorinated molecules.

中文翻译：

由相同前体控制合成 α-CF2H 或 α-CF2Cl 苯乙烯：3,3-二氟烯丙基肼的脱肼氢化或氯化

通过仔细选择反应条件，我们开发了可控的FeCl ₃ - 或CuCl ₂介导的3,3-二氟烯丙基肼的脱肼氢化或氯化反应以得到α-CF ₂ H或α-CF ₂ Cl苯乙烯。目前的反应首次提供了一种从相同前驱体开始直接选择性合成α-CF ₂ H和α-CF ₂ Cl苯乙烯的简便方法，该方法易于放大，并显示出广泛的底物范围和良好的性能。官能团耐受性。此外，产物衍生化实验表明，所得的α-CF ₂Cl苯乙烯是用于氟化分子多样化合成的实用且多用途的结构单元。

更新日期：2023-06-01

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