New Mixed-Donor Bidentate Ligands Based on N-Heterocyclic Carbene and Thione Donors

Miriam Slivarichova, Ruaa Ahmad, Yu-King Kuo, Joshua Nunn, Mairi F. Haddow, Hafiizah Othman, Gareth Owen

Research output: Contribution to journalArticlepeer-review


A new family of mixed-donor bidentate ligands containing both N-heterocyclic carbene (NHC) and thione functionalities is reported. The imidazolium salt precursors 1,1′-methylene(3-R-imidazol-2-ylidene)(3-R-2H-imidazole-2-thione) [CSRH] halide (where R = methyl, benzyl; halide = bromide, iodide) have been synthesized. Their coordination to copper(I) salts has been explored, providing the complexes [Cu(CSR)X]2 (where R = methyl, benzyl; halide = bromide, iodide). Structural characterization of two of the complexes confirmed the dimeric nature of these complexes in the solid state but revealed different coordination modes for each case (κ1-C, κ1-S, μ-S and κ1-C, κ1-S). Solutions of the copper complexes slowly react with oxygen under aerobic conditions to form uncoordinated 1,1′-methylene(3-R-2H-imidazol-2-one)(3-R-2H-imidazole-2-thione), SOR (where R = methyl, benzyl), where the NHC moiety has been converted into a urea functional group. The complexes were investigated as candidates in copper-catalyzed cross-coupling reactions.
Original languageEnglish
Pages (from-to)4779-4787
Issue number17
Publication statusPublished - 11 Aug 2011


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