Authors: Brieger, Lukas
Schrimpf, Tobias
Scheel, Rebecca
Unkelbach, Christian
Strohmann, Carsten
Title: Towards substrate-reagent interaction of Lochmann-Schlosser bases in THF: bridging THF hides potential reaction site of a chiral superbase
Language (ISO): en
Abstract: The 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.
Subject Headings: Alkali metals
X-ray diffraction
Issue Date: 2022-09-13
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Appears in Collections:Lehrstühle für Anorganische Chemie

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