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...

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Veröffentlicht in:Journal of organic chemistry 2021-09, Vol.86 (18), p.13111-13117
Hauptverfasser: Luo, Siyi, Peng, Marie, Querard, Pierre, Li, Chen-Chen, Li, Chao-Jun
Format: Artikel
Sprache:eng
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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