Applications of Transition Metal-Catalyzed ortho-Fluorine-Directed C–H Functionalization of (Poly)fluoroarenes in Organic Synthesis

IF 51.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Chemical Reviews Pub Date : 2024-04-02 DOI:10.1021/acs.chemrev.3c00793
Yudha P. Budiman*, Robin N. Perutz*, Patrick G. Steel*, Udo Radius* and Todd B. Marder*, 
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Abstract

The synthesis of organic compounds efficiently via fewer steps but in higher yields is desirable as this reduces energy and reagent use, waste production, and thus environmental impact as well as cost. The reactivity of C–H bonds ortho to fluorine substituents in (poly)fluoroarenes with metal centers is enhanced relative to meta and para positions. Thus, direct C–H functionalization of (poly)fluoroarenes without prefunctionalization is becoming a significant area of research in organic chemistry. Novel and selective methodologies to functionalize (poly)fluorinated arenes by taking advantage of the reactivity of C–H bonds ortho to C–F bonds are continuously being developed. This review summarizes the reasons for the enhanced reactivity and the consequent developments in the synthesis of valuable (poly)fluoroarene-containing organic compounds.

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有机合成中过渡金属催化的正氟导向(多)氟烯 C-H 功能化的应用
通过更少的步骤但更高的产量高效合成有机化合物是可取的,因为这样可以减少能源和试剂的使用、废物的产生,从而减少对环境的影响并降低成本。与金属中心相比,(多)氟烯中氟取代基正位的 C-H 键的反应活性更强。因此,在不进行预官能化的情况下直接对(多)氟烯进行 C-H 官能化正在成为有机化学研究的一个重要领域。利用 C-H 键与 C-F 键正交的反应活性,使(多)氟烯烃官能化的新型选择性方法正在不断开发中。本综述总结了反应活性增强的原因,以及在合成有价值的含(多)氟烯有机化合物方面随之取得的进展。
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来源期刊
Chemical Reviews
Chemical Reviews 化学-化学综合
CiteScore
106.00
自引率
1.10%
发文量
278
审稿时长
4.3 months
期刊介绍: Chemical Reviews is a highly regarded and highest-ranked journal covering the general topic of chemistry. Its mission is to provide comprehensive, authoritative, critical, and readable reviews of important recent research in organic, inorganic, physical, analytical, theoretical, and biological chemistry. Since 1985, Chemical Reviews has also published periodic thematic issues that focus on a single theme or direction of emerging research.
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