Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction
| Autor: | John C. Widen, Sarah M. Wells, Daniel A. Harki, Kay M. Brummond |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Proline
Alkyne 010402 general chemistry 01 natural sciences Biochemistry Article chemistry.chemical_compound Polymer chemistry Organic chemistry Molecule Sulfhydryl Compounds Physical and Theoretical Chemistry chemistry.chemical_classification Carbon Monoxide Molecular Structure Limiting reagent Hydroxyl Radical 010405 organic chemistry Organic Chemistry Nicholas reaction Cobalt 0104 chemical sciences Pargyline chemistry Alkynes Propargyl Hydroxyl radical Ligation |
| Zdroj: | Organic Letters. 18:4566-4569 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The Nicholas reaction has been applied to the installation of alkyne ligation handles. Acid-promoted propargylation of hydroxyl, sulfhydryl, amino, and carboxyl groups using dicobalt hexacarbonyl-stabilized propargylium ions is reported within. This method is especially useful for the introduction of propargyl groups into base-sensitive molecules, thereby expanding the toolbox of methods for the incorporation of alkynes for bioorthogonal reactions. High-value molecules are used as the limiting reagent and various propargylium ion precursors are compared. |
| Databáze: | OpenAIRE |
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