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Upgrading ketone synthesis direct from carboxylic acids and organohalides.
Nature Communications ( IF 14.7 ) Pub Date : 2020-07-03 , DOI: 10.1038/s41467-020-17224-2
Rehanguli Ruzi 1 , Kai Liu 1 , Chengjian Zhu 1, 2 , Jin Xie 1
Affiliation  

The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals.



中文翻译:

直接从羧酸和有机卤化物升级酮的合成。

酮官能团在有机化学中具有独特的反应性,并与许多有用的反应有关。酮合成的催化方法正在不断发展。在这里,我们报告了光氧化还原,镍和磷烷基自由基交叉交叉亲电偶联的市售化学品,芳香酸和芳基/烷基溴化物。这允许直接合成高度官能化的酮,而无需制备活化的羰基中间体或有机金属化合物,从而补充了常规的Weinreb酮合成。使用合适的光催化剂,配体量和溶剂可以匹配任何简单催化循环所需的反应速率。

更新日期:2020-07-03
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