Towards substrate-reagent interaction of Lochmann-Schlosser bases in THF: bridging THF hides potential reaction site of a chiral superbase

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dc.contributor.authorBrieger, Lukas
dc.contributor.authorSchrimpf, Tobias
dc.contributor.authorScheel, Rebecca
dc.contributor.authorUnkelbach, Christian
dc.contributor.authorStrohmann, Carsten
dc.date.accessioned2024-01-10T14:40:57Z
dc.date.available2024-01-10T14:40:57Z
dc.date.issued2022-09-13
dc.description.abstractThe metalation of N,N-dimethylaminomethylferrocene in THF by the superbasic mixture of nBuLi/KOtBu proceeds readily at low temperatures to afford a bimetallic Li2K2 aggregate containing ferrocenyl anions and tert-butoxide. Starting from an enantiomerically enriched ortho-lithiated aminomethylferrocene, an enantiomerically pure superbase can be prepared. The molecular compound exhibits superbasic behavior deprotonating N,N-dimethylbenzylamine in the α-position and is also capable of deprotonating toluene. Quantum chemical calculations provide insight into the role of the bridging THF molecule to the possible substrate–reagent interaction. In addition, a benzylpotassium alkoxide adduct gives a closer look into the corresponding reaction site of the Lochmann–Schlosser base that is reported herein.en
dc.identifier.urihttp://hdl.handle.net/2003/42272
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-24109
dc.language.isoende
dc.relation.ispartofseriesChemistry - a European journal;28(69)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/de
dc.subjectAlkali metalsen
dc.subjectChiralityen
dc.subjectLithiumen
dc.subjectPotassiumen
dc.subjectX-ray diffractionen
dc.subject.ddc540
dc.titleTowards substrate-reagent interaction of Lochmann-Schlosser bases in THF: bridging THF hides potential reaction site of a chiral superbaseen
dc.typeTextde
dc.type.publicationtypeResearchArticlede
dcterms.accessRightsopen access
eldorado.secondarypublicationtruede
eldorado.secondarypublication.primarycitationL. Brieger, T. Schrimpf, R. Scheel, C. Unkelbach, C. Strohmann, Chem. Eur. J. 2022, 28, e202202660.de
eldorado.secondarypublication.primaryidentifierDOI https://doi.org/10.1002/chem.202202660de

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