Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos)
| Autor: | Daniel Sowa Prendes, Maurice Paaßen, Viktoria H. Gessner, Ilja Rodstein, Leon Wickert |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Steric effects Reaction conditions Primary (chemistry) 010405 organic chemistry education Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Article humanities Coupling reaction 0104 chemical sciences 3. Good health Catalysis chemistry Ylide Alkyl |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c01771 |
| Popis: | Ylide-substituted phosphines have been shown to be excellent ligands for C–N coupling reactions under mild reaction conditions. Here we report studies on the impact of the steric demand of the substituent in the ylide-backbone on the catalytic activity. Two new YPhos ligands with bulky ortho-tolyl (pinkYPhos) and mesityl (mesYPhos) substituents were synthesized, which are slightly more sterically demanding than their phenyl analogue but considerably less flexible. This change in the ligand design leads to higher selectivities and yields in the arylation of small primary amines compared to previously reported YPhos ligands. Even MeNH2 and EtNH2 could be coupled at room temperature with a series of aryl chlorides in high yields. |
| Databáze: | OpenAIRE |
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