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Issue 72, 2016
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Activation of C–F bonds in fluoroarenes by N-heterocyclic carbenes as an effective route to synthesize abnormal NHC complexes

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Abstract

IPr (1a) reacts with octafluorotoluene by an unexpected sequential substitution of fluorides in two separate rings. The resulting tetrasubstituted imidazolium salt was isolated and elaborated into Ag(I) and Au(I) complexes with a novel abnormal NHC ligand. Both IPr (1a) and IMes (1b) were also found to be moderately reactive by nucleophilic substitution of the aromatic C–F bond in a weakly-activated fluoroarene, 1-fluoro-4-trifluoromethylbenzene (5).

Graphical abstract: Activation of C–F bonds in fluoroarenes by N-heterocyclic carbenes as an effective route to synthesize abnormal NHC complexes

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Article information


Submitted
11 Jun 2016
Accepted
11 Aug 2016
First published
11 Aug 2016

Chem. Commun., 2016,52, 10922-10925
Article type
Communication

Activation of C–F bonds in fluoroarenes by N-heterocyclic carbenes as an effective route to synthesize abnormal NHC complexes

Y. Kim and E. Lee, Chem. Commun., 2016, 52, 10922
DOI: 10.1039/C6CC04896J

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