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Publication - Dr Natalie Pridmore

    Outer-Sphere Electrophilic Fluorination of Organometallic Complexes

    Citation

    Milner, LM, Pridmore, NE, Whitwood, AC, Lynam, JM & Slattery, JM, 2015, ‘Outer-Sphere Electrophilic Fluorination of Organometallic Complexes’. Journal of the American Chemical Society, vol 137., pp. 10753-10759

    Abstract

    Organofluorine chemistry plays a key role in materials science, pharmaceuticals, agrochemicals, and medical imaging. However, the formation of new carbon-fluorine bonds with controlled regiochemistry and functional group tolerance is synthetically challenging. The use of metal complexes to promote fluorination reactions is of great current interest, but even state-of-the-art approaches are limited in their substrate scope, often require activated substrates, or do not allow access to desirable functionality, such as alkenyl C(sp2)-F or chiral C(sp3)-F centers. Here, we report the formation of new alkenyl and alkyl C-F bonds in the coordination sphere of ruthenium via an unprecedented outer-sphere electrophilic fluorination mechanism. The organometallic species involved are derived from nonactivated substrates (pyridine and terminal alkynes), and C-F bond formation occurs with full regio- and diastereoselectivity. The fluorinated ligands that are formed are retained at the metal, which allows subsequent metal-mediated reactivity.

    Full details in the University publications repository