Brieger, LukasUnkelbach, ChristianStrohmann, Carsten2022-03-152022-03-152021-10-11http://hdl.handle.net/2003/4079410.17877/DE290R-22651The incorporation of heavy alkali metals into substrates is both challenging and essential for many reactions. Here, we report the formation of THF-solvated alkali metal benzyl compounds [PhCH2M ⋅ (thf)n] (M=Na, Rb, Cs). The synthesis was carried out by deprotonation of toluene with the bimetallic mixture n-butyllithium/alkali metal tert-butoxide and selective crystallization from THF of the defined benzyl compounds. Insights into the molecular structure in the solid as well as in solution state are gained by single crystal X-ray experiments and NMR spectroscopic studies. The compounds could be successfully used as alkali metal mediating reagents. The example of caesium showed the convenient use by deprotonating acidic C−H as well as N−H compounds to gain insight into the aminometalation using these reagents.enChemistry - a European journal;27(71)https://creativecommons.org/licenses/by/4.0/Alkali metalsCarbanionsHydroaminationMain group elementsOrganometallic chemistry540article (journal)