Angewandte Chemie International Edition · 2013 · 2.5K citations · 904 references
Natural SciencesChemistryMedicinal ChemistryCatalysisDrug DiscoveryInorganic ChemistryChemical Space ExplorationCoordination ChemistryFluorination ProcessesFluorine ChemistryHydration Free EnergyTransition-metal-catalyzed Functionalization
Over the past decade, organo‑ and transition‑metal catalysis have driven major conceptual advances in fluorination, yet challenges remain in forming the parent C–F bond due to high hydration energy, strong metal–fluorine bonds, and highly polarized bonds to fluorine, and many fluorination reactions still lack generality, predictability, and cost‑efficiency. This review aims to summarize conventional fluorination reactions and highlight modern developments in the field. It focuses on reactions that introduce fluorinated functional groups, emphasizing recent advances enabled by organo‑ and transition‑metal catalysis. Modern fluorination methods have made fluorinated molecules more readily available than ever, impacting areas such as drug discovery and positron emission tomography even with limited material quantities.
Abstract Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo‐ and transition‐metal catalysis. The most challenging transformation remains the formation of the parent CF bond, primarily as a consequence of the high hydration energy of fluoride, strong metal—fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost‐efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.
904
van der Waals Volumes and Radii
A. Bondì · The Journal of Physical Chemistry · 1964 · 19.2K citations
The Many Roles for Fluorine in Medicinal Chemistry
William K. Hagmann · Journal of Medicinal Chemistry · 2008 · 3.6K citations · Full text
James T. Lindley · Tetrahedron · 1984 · 2.2K citations
Thomas D. Penning, John J. Talley, Stephen R. Bertenshaw et al. · Journal of Medicinal Chemistry · 1997 · 2K citations · Full text