Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 71, Pages 17780-17784Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103430
Keywords
alkali metals; carbanions; hydroamination; main group elements; organometallic chemistry
Categories
Funding
- Fonds der Chemischen Industrie (FCI)
- Projekt DEAL
Ask authors/readers for more resources
The formation of THF-solvated alkali metal benzyl compounds [PhCH2M . (thf)(n)] (M=Na, Rb, Cs) was successfully achieved through deprotonation of toluene with a bimetallic mixture and selective crystallization. These compounds can serve as alkali metal mediating reagents and have shown to be convenient for deprotonating acidic C-H as well as N-H compounds for aminometalation.
The 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available