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

Dalton Transactions : an International Journal of Inorganic Chemistry
Laure BenhamouVincent César

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 Rh(I)(COD) fragment allows the isolation of complex 7 displaying a rarely observed four-membered NHC-containing metallacycle and an enforced η(1)-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.

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Citations

Jul 1, 2014·Organic & Biomolecular Chemistry·Alexander F KhlebnikovMikhail S Novikov
Jan 14, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Marta Roselló-Merino, Stephen M Mansell
Jul 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Charlotte ThieUlrich Siemeling
Aug 7, 2019·Chemistry : a European Journal·Idir BenaissaVincent César

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