In this presentation, we report on an unusual synthetic pathway involving dihydrophenazines that allowed us to isolate the up-to-now elusive N,N'-dimesitylbenzimidazol-2-ylidene (BMes ). The dimer of N,N'-di(o-tolyl)benzimidazol-2-ylidene (BTol ) was also prepared. The stereoelectronic properties of these two N-heterocyclic carbenes (NHCs) were determined from the corresponding [RhCl(cod)(NHC)] or [RhCl(CO)2(NHC)] complexes. The catalytic activity of the [RuCl2(=CHPh)(PCy3)(NHC)] complexes derived from BMes  and BTol  was evaluated in the ring-closing metathesis of a,?-dienes and compared to various reference complexes using standard experimental procedures.

Synthesis of new benzimidazolylidene derivatives and their use as ligands in ruthenium-promoted olefin metathesis

244th National Meeting (2012)

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