Unlocking the Potential of Phenacyl Protecting Groups: CO2-Based Formation and Photocatalytic Release of Caged Amines
| Autor: | Elisabeth Speckmeier, Michael Klimkait, Kirsten Zeitler |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Primary (chemistry) 010405 organic chemistry Organic Chemistry 010402 general chemistry Phenacyl Ascorbic acid Highly selective 01 natural sciences Combinatorial chemistry 0104 chemical sciences Amino acid Carbamate esters chemistry.chemical_compound chemistry Photocatalysis Acetonitrile |
| Zdroj: | The Journal of Organic Chemistry. 83:3738-3745 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.8b00096 |
| Popis: | Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|