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Issue 6, 2014
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Carbon–fluorine bond cleavage in fluoroarenes via a niobium(iii) imido complex: from stoichiometric to catalytic hydrodefluorination

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Abstract

The mechanism of activation of C–F bonds in fluoroarenes using a well-defined niobium(III) imido complex has been investigated. The Nb(III) arene species [BDI]Nb(NtBu)(η6-C6H6), 1, (BDI = β-diketimate), reacts stoichiometrically with fluoroarenes to yield niobium(V) aryl fluorides. Spectroscopic analysis supported by DFT calculations revealed the critical involvement of a Nb(III) fluoroarene-bound species. In contrast to previous reports of related reactivity, we found that perfluorinated arenes (i.e. those normally assumed to bear more ‘activated’ C–F bonds) are, in the present system, much less reactive towards C–F bond cleavage than mono- or difluoro-substituted arenes. In addition to demonstrating stoichiometric hydrodefluorination reactions, we also describe an efficient and mild hydrodefluorination of mono- and di-fluoroarenes that is catalytic in niobium.

Graphical abstract: Carbon–fluorine bond cleavage in fluoroarenes via a niobium(iii) imido complex: from stoichiometric to catalytic hydrodefluorination

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Supplementary files

Article information


Submitted
01 Jan 2014
Accepted
04 Apr 2014
First published
04 Apr 2014

Chem. Sci., 2014,5, 2517-2524
Article type
Edge Article

Carbon–fluorine bond cleavage in fluoroarenes via a niobium(III) imido complex: from stoichiometric to catalytic hydrodefluorination

T. L. Gianetti, R. G. Bergman and J. Arnold, Chem. Sci., 2014, 5, 2517
DOI: 10.1039/C4SC00006D

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