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Copper-Catalyzed Conjugate Addition of Carbonyls as Carbanion Equivalent via Hydrazones
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-09-03 , DOI: 10.1021/acs.joc.1c01380
Siyi Luo 1 , Marie Peng 1 , Pierre Querard 1 , Chen-Chen Li 1 , Chao-Jun Li 1
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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%.

中文翻译:

铜催化的羰基化合物通过腙作为碳负离子等价物的共轭加成

铜催化的共轭加成是形成新碳-碳键的经典方法。然而,铜从未在腙化学中显示出对umpolung 碳负离子的催化活性。在此,我们报告了在室温下由容易获得的铜配合物催化的腙的轻松共轭加成。甲基铜(I)和富电子膦双齿配体的使用是影响反应性的关键因素。该反应允许各种芳族腙与各种共轭化合物反应,以约 20% 至 99% 的产率生成 1,4-加合物。
更新日期:2021-09-17
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