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RESEARCH PRODUCT
Aminomethyl-Substituted Ferrocenes and Derivatives: Straightforward Synthetic Routes, Structural Characterization, and Electrochemical Analysis
Daoud NaoufalRidha Ben SalemFatima AllouchNejib DwadniaDominique LucasJulien RogerCharles H. DevillersMarie-josée PenouilhNadine PirioHélène CatteySophie FournierJean-cyrille HiersoJean-cyrille Hiersosubject
Steric effectsNitromethaneReducing agentChemistryOrganic ChemistryElectrochemistryReductive aminationCombinatorial chemistryInorganic Chemistrychemistry.chemical_compoundFerroceneOrganic chemistryFerrocene derivativesPhysical and Theoretical ChemistryCyclic voltammetrydescription
A variety of aminomethyl-substituted ferrocenes and the parent compounds (iminomethyl)ferrocenes, azaferrocenophanes, and diferrocenylamines can be selectively synthesized from reductive amination of 1,1′-diformylferrocene or formylferrocene. The optimized one- or two-step reactions have delivered 13 new compounds, isolated in 65–97% yields, which include tertiary (ferrocenylmethyl)amines and azaferrocenophanes by using NaBH(OAc)3 as a mild reducing agent and (iminomethyl)ferrocenes and secondary (ferrocenylmethyl)amines by using LiAlH4. X-ray structures of representative members of these ferrocene derivative families have evidenced the preferred conformation adopted by ferrocene backbones, in which surprisingly the steric hindrance is apparently not systematically minimized. 15N NMR measurements on aminomethyl-substituted ferrocenes and derivatives are provided for the first time, establishing benchmark values ranging from −330 to −305 ppm (nitromethane δ 0 ppm). The cyclic voltammetry of these species e...
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-06-19 | Organometallics |