Ruthenium catalysts bearing a benzimidazolylidene ligand for the metathetical ring-closure of tetrasubstituted cycloolefins

Dalton Transactions : an International Journal of Inorganic Chemistry
Yannick BorguetLionel Delaude

Abstract

Deprotonation of 1,3-di(2-tolyl)benzimidazolium tetrafluoroborate with a strong base afforded 1,3-di(2-tolyl)benzimidazol-2-ylidene (BTol), which dimerized progressively into the corresponding dibenzotetraazafulvalene. The complexes [RhCl(COD)(BTol)] (COD is 1,5-cyclooctadiene) and cis-[RhCl(CO)2(BTol)] were synthesized to probe the steric and electronic parameters of BTol. Comparison of the percentage of buried volume (%VBur) and of the Tolman electronic parameter (TEP) of BTol with those determined previously for 1,3-dimesitylbenzimidazol-2-ylidene (BMes) revealed that the two N-heterocyclic carbenes displayed similar electron donicities, yet the 2-tolyl substituents took a slightly greater share of the rhodium coordination sphere than the mesityl groups, due to a more pronounced tilt. The anti,anti conformation adopted by BTol in the molecular structure of [RhCl(COD)(BTol)] ensured nonetheless a remarkably unhindered access to the metal center, as evidenced by steric maps. Second-generation ruthenium-benzylidene and isopropoxybenzylidene complexes featuring the BTol ligand were obtained via phosphine exchange from the first generation Grubbs and Hoveyda-Grubbs catalysts, respectively. The atropisomerism of the 2-tolyl substi...Continue Reading

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Citations

Sep 24, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ileana DragutanAlbert Demonceau
Feb 24, 2016·Inorganic Chemistry·Dani SetiawanDieter Cremer
Nov 27, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Veronica ParadisoFabia Grisi
Mar 30, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Dieter Cremer, Elfi Kraka

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