Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 27, Pages 7986-7991Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801530
Keywords
carbene ligands; electronic communication; manganese; N-heterocyclic carbenes; oxidative coupling
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Funding
- Centre National de la Recherche Scientifique (CNRS, France)
- French Embassy in Moscow
- RUDN University program 5-100
- Russian Scientific Foundation [14-13-00801]
- Ministry of Education and Science of the Russian Federation [RFMEFI61917X0007]
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The oxidative coupling of anionic imidazol-4-ylidenes protected at the C2 position with [MnCp(CO)(2)] or BH3 led to the corresponding 4,4'-bis(2H-imidazol-2-ylidene) complexes or adducts, in which the two carbene moieties are connected through a single C-C bond. Subsequent acidic treatment of the later species led to the corresponding 4,4'-bis(imidazolium) salts in good yields. The overall procedure offers practical access to a novel class of Janus-type bis(NHC)s. Strikingly, the coplanarity of the two NHC rings within the mesityl derivative 4,4'-bis(IMes), favored by steric hindrance along with stabilizing intramolecular C-H center dot center dot center dot pi aryl interactions, allows the alignment of the pi-systems and, as a direct consequence, significant electron communication through the bis(carbene) scaffold.
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