6533b86ffe1ef96bd12cdb78

RESEARCH PRODUCT

Converging and Diverging Synthetic Strategies to Tetradentate (N,N′)-Diaminomethyl,(P,P′)-Ferrocenyl Ligands: Influence of tert-Butyl Groups on Ferrocene Backbone Conformation

Daoud NaoufalFatima AllouchHélène CatteyNejib DwadniaMarie-josé PenouilhNikolay V. VologdinNadine PirioJulien RogerJean-cyrille HiersoJean-cyrille HiersoRidha Ben SalemYurii V. Svyaschenko

subject

Tert butylchemistry.chemical_classificationStereochemistryArylOrganic ChemistryBackbone conformationInorganic Chemistrychemistry.chemical_compoundchemistryFerroceneCyclopentadienyl complexDiphosphinesSurface modificationPhysical and Theoretical ChemistryAlkyl

description

Hexasubstituted hybrid tetradentate (N,N′,P,P′)-ferrocenes bearing phosphino and aminomethyl groups, plus hindering tert-butyl moieties, were synthesized by using two different strategies: a “diverging” synthesis involving successive functionalization of preformed di-tert-butylated ferrocene and a “converging” assembly of the species from appropriately substituted cyclopentadienyl rings. While the new cyclopentadienyl salts formed are of interest, their assembly with iron dichloride used as a “converging” way to produce tetradentate ferrocene ligands presented several drawbacks. Conversely, the synthesis of new tert-butylated (aminomethyl)ferrocene derivatives was found convenient to further form (N,N′)-aminomethyl,(P,P′)-tert-butylated-ferrocenyl diphosphines by N-directed ortho-metalation. The novel N2-didentate and N2P2-tetradentate tert-butylated ferrocene compounds were all synthesized in good to high yields (48–96%) and tolerated aryl, alkyl, and heteroaryl phosphino groups as substituents on nitrog...

yearjournalcountryeditionlanguage
2015-10-02Organometallics
https://doi.org/10.1021/acs.organomet.5b00601