Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos) .
| Autor: | Rodstein I; Faculty of Chemistry and Biochemistry, Chair of Inorganic Chemistry II, Ruhr University Bochum, Universitätsstr. 150, 44801 Bochum, Germany., Prendes DS; Faculty of Chemistry and Biochemistry, Chair of Inorganic Chemistry II, Ruhr University Bochum, Universitätsstr. 150, 44801 Bochum, Germany., Wickert L; Faculty of Chemistry and Biochemistry, Chair of Inorganic Chemistry II, Ruhr University Bochum, Universitätsstr. 150, 44801 Bochum, Germany., Paaßen M; Faculty of Chemistry and Biochemistry, Chair of Inorganic Chemistry II, Ruhr University Bochum, Universitätsstr. 150, 44801 Bochum, Germany., Gessner VH; Faculty of Chemistry and Biochemistry, Chair of Inorganic Chemistry II, Ruhr University Bochum, Universitätsstr. 150, 44801 Bochum, Germany. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2020 Nov 20; Vol. 85 (22), pp. 14674-14683. Date of Electronic Publication: 2020 Sep 21. |
| DOI: | 10.1021/acs.joc.0c01771 |
| Abstrakt: | 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 MeNH |
| Databáze: | MEDLINE |
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