Copper-Catalyzed Conjugate Addition of Carbonyls as Carbanion Equivalent via Hydrazones
Copper-catalyzed conjugate addition is a classic method for forming new carbon–carbon bonds. However, copper has never showed catalytic activity for umpolung carbanions in hydrazone chemistry. Herein, we report a facile conjugate addition of hydrazone catalyzed by readily available copper complexes...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2021-09, Vol.86 (18), p.13111-13117 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Copper-catalyzed conjugate addition is a classic method for forming new carbon–carbon bonds. However, copper has never showed catalytic activity for umpolung carbanions in hydrazone chemistry. Herein, we report a facile conjugate addition of hydrazone catalyzed by readily available copper complexes at room temperature. The employment of mesitylcopper(I) and electron-rich phosphine bidentate ligand is a key factor affecting reactivity. The reaction allows various aromatic hydrazones to react with diverse conjugated compounds to produce 1,4-adducts in yields of about 20 to 99%. |
---|---|
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c01380 |