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

Budiman, Yudha P.; Perutz, Robin N.; Steel, Patrick G.; Radius, Udo; Marder, Todd B.

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.

Citation

Budiman, Y. P., Perutz, R. N., Steel, P. G., Radius, U., & Marder, T. B. (2024). Applications of Transition Metal-Catalyzed ortho-Fluorine-Directed C–H Functionalization of (Poly)fluoroarenes in Organic Synthesis. Chemical Reviews, 124(8), 4822-4862. https://doi.org/10.1021/acs.chemrev.3c00793

• Journal Article Type: Article
• Acceptance Date: Feb 22, 2024
• Online Publication Date: Apr 2, 2024
• Publication Date: Apr 24, 2024
• Deposit Date: Apr 4, 2024
• Publicly Available Date: Apr 4, 2024
• Journal: Chemical Reviews
• Print ISSN: 0009-2665
• Electronic ISSN: 1520-6890
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 124
• Issue: 8
• Pages: 4822-4862
• DOI: https://doi.org/10.1021/acs.chemrev.3c00793
• Keywords: General Chemistry
• Public URL: https://durham-repository.worktribe.com/output/2375997