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Copper‐mediated Synthesis of N‐Aryl‐oxamic Acids.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2024-07-25 , DOI: 10.1002/chem.202402298
Margaux Badufle 1 , Frédéric Robert 1 , Yannick Landais 2
Affiliation  

The Cu‐catalyzed Ullmann‐Goldberg cross‐coupling between aryl iodides and oxamates is shown to afford the corresponding N‐aryloxamates with yields ranging from moderate to excellent, when the oxamate precursor incorporates a bulky tertiary alkyl group effectively preventing product degradation under the strongly basic reaction conditions. The final oxamic acids are then generated through the acid hydrolysis of the oxamate in high yields. These acids were then converted into urethanes using PIDA under thermal conditions or a visible‐light Fe‐LMCT process. While electron‐deficient N‐aryl oxamic acids provide urethanes with high efficiencies, electron‐rich counterparts led to diminished yields due to aryl group over‐oxidation induced by PIDA.

中文翻译:


N-芳基-肟酸的铜介导合成。



当草酸酯前体包含大叔烷基时,芳基碘化物和草酸酯之间的 Cu 催化 Ullmann-Goldberg 交叉偶联可产生相应的 N-芳基草酸酯,产率从中等到优异,此时草酸酯前体包含大体积的叔烷基,有效防止强碱性下的产物降解。反应条件。然后通过草酸盐的酸水解以高产率生成最终的草酸盐。然后使用 PIDA 在热条件下或可见光 Fe-LMCT 过程中将这些酸转化为聚氨酯。虽然缺电子的 N-芳基肟酸为聚氨酯提供了高效率,但富电子的 N-芳基肟酸由于 PIDA 引起的芳基过度氧化而导致产率下降。
更新日期:2024-07-25
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