Synthesis of a Water-Soluble Tridentate (Dimethylamino)ethyl Cu(I)/Cu(II)-Ligand
| Autor: | Jörg Pietruszka, T. Moritz Weber |
|---|---|
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Synthesis. |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/a-2034-9427 |
| Popis: | Copper-catalyzed alkyne azide click chemistry (CuAAC) plays an important role in drug development and labeling of biological materials. Stabilizing ligands prevent Cu(I)-species from oxidation, increases the solubility of copper, and increases the acceleration of the catalyzed process. In this context, we report on the synthesis of a tris-amine tridentate Cu-ligand (TDETA), with terminal (dimethylamino)ethyl-substitution, which can be legally synthesized as a replacement of toxic nitrogen mustard HN3 as an intermediate and is a scalable alternative to the previously found amine ligand DTEA. The class II ligand TDETA exhibits excellent solubility properties in organic solvents and aqueous solutions, outcompetes the commercial class I ligands THPTA and TBTA for a broad range of azide and alkyne combinations using Cu(I)- and Cu(II)-species, and was shown to be recoverable in a yield of 80%. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|