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Issue 11, 2014
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Metal-assisted conversion of an N-ylide mesomeric betaine into its carbenic tautomer: generation of N-(fluoren-9-yl)imidazol-2-ylidene complexes

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Abstract

Whereas the N-ylide mesomeric betaine 2, consisting of a fluorenyl anion directly attached to an imidazolium ring, is not in equilibrium with its putative free N-(fluoren-9-yl)imidazol-2-ylidene tautomer, its reaction with a metallic centre induces its interconversion to yield the corresponding monoligated N-heterocyclic carbene complex (Au(I) and Rh(I)). Deprotonation of 2 and coordination to the RhI(COD) fragment allows the isolation of complex 7 displaying a rarely observed four-membered NHC-containing metallacycle and an enforced η1-fluorenyl ligand. Upon reaction with CpFe(CO)2I precursor, insertion of a carbonyl ligand into the Fe–fluorenyl bond occurs and yields the acyl–Fe complex 8.

Graphical abstract: Metal-assisted conversion of an N-ylide mesomeric betaine into its carbenic tautomer: generation of N-(fluoren-9-yl)imidazol-2-ylidene complexes

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Article information


Submitted
31 Oct 2013
Accepted
03 Dec 2013
First published
04 Dec 2013

Dalton Trans., 2014,43, 4474-4482
Article type
Paper

Metal-assisted conversion of an N-ylide mesomeric betaine into its carbenic tautomer: generation of N-(fluoren-9-yl)imidazol-2-ylidene complexes

L. Benhamou, S. Bastin, N. Lugan, G. Lavigne and V. César, Dalton Trans., 2014, 43, 4474
DOI: 10.1039/C3DT53089B

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