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From ferrocene to fluorine-containing penta-substituted derivatives and all points in-between; or, how to increase the available chemical space

Abstract : In spite of the growing interest in fluorine-containing compounds, and the improvements in materials, optical and biological properties that can arise from substitution of a phenyl ring by ferrocene within a molecular scaffold, synthetic strategies that allow the efficient preparation of fluoroferrocene derivatives are scarce. Following conversion of ferrocene to fluoroferrocene, we have developed routes to fluorine-containing di-, tri-, tetra- and penta-substituted ferrocene derivatives to extend the available chemical space. Our approach is based on the identification of suitable reagents and conditions to achieve fluorine-directed deprotometalation, and exploitation of the halogen 'dance' rearrangement in the ferrocene series.
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Mehdi Tazi, William Erb, Thierry Roisnel, Vincent Dorcet, Florence Mongin, et al.. From ferrocene to fluorine-containing penta-substituted derivatives and all points in-between; or, how to increase the available chemical space. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2019, 17 (42), pp.9352-9359. ⟨10.1039/c9ob01885a⟩. ⟨hal-02364875⟩

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