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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

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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.

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

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Publication details

The article was received on 27 Aug 2019, accepted on 08 Oct 2019 and first published on 08 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01885A
Org. Biomol. Chem., 2019, Advance Article

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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

    M. Tazi, W. Erb, T. Roisnel, V. Dorcet, F. Mongin and P. J. Low, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01885A

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