Oxidative coupling of anionic abnormal N-Heterocyclic carbenes: Efficient access to Janus-type 4,4′-bis(2H-imidazol-2-ylidene)s - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2018

Oxidative coupling of anionic abnormal N-Heterocyclic carbenes: Efficient access to Janus-type 4,4′-bis(2H-imidazol-2-ylidene)s

Résumé

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⋅⋅⋅π aryl interactions, allows the alignment of the π-systems and, as a direct consequence, significant electron communication through the bis(carbene) scaffold.
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Dates et versions

hal-01948415 , version 1 (07-12-2018)

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Alina A Grineva, Dmitry A. Valyaev, Vincent César, O. A. Filippov, Victor N. Khrustalev, et al.. Oxidative coupling of anionic abnormal N-Heterocyclic carbenes: Efficient access to Janus-type 4,4′-bis(2H-imidazol-2-ylidene)s. Angewandte Chemie International Edition, 2018, 57 (27), pp.7986-7991. ⟨10.1002/anie.201801530⟩. ⟨hal-01948415⟩
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