Towards the Stable Binding of Mercury: Synthesis and Functionalization of Dibenzyldiazabicyclononane Scaffolds
Research output: Contribution to journal › Research article › Contributed › peer-review
Contributors
Abstract
A universally applicable synthesis route for the preparation of functionalized diazabicyclononane compounds was elaborated starting from a readily available 1,5-diphenyl-3,7-diazabicyclo[3.3.1] nonan-9-ol by alkylation of both secondary amines with modified benzyl residues containing a bromo, trimethylstannyl, trimethylsilyl, and pinacolboranyl residue. High yields (65–88 %) were achieved, supporting the intended purpose of these compounds: efficient mercuration reactions to stably bind Hg2+. Finally, the C-9 position of two functionalized diazabicyclononanes was further modified by introducing an azide functionality. This enables the conjugation to biomolecules of interest via click chemistry combined with a tracking by the introduced mercury isotopes.
Details
| Original language | English |
|---|---|
| Article number | e202400258 |
| Journal | European Journal of Organic Chemistry |
| Volume | 27 |
| Issue number | 25 |
| Publication status | Published - 1 Jul 2024 |
| Peer-reviewed | Yes |
Keywords
ASJC Scopus subject areas
Keywords
- bispidine skeleton, ligand design, mercuration, organomercury compounds