N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Aldehydes under Continuous Flow Conditions,Advanced Synthesis & Catalysis

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N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Aldehydes under Continuous Flow Conditions
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-05-09 , DOI: 10.1002/adsc.202200124
Bence S. Nagy ₁ , C. Oliver Kappe ₁ , Sandor Otvos ₁

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The efficacy of synthetic methodologies is based not only on potent chemistries but also on processing strategies that amplify reaction performance and overall safety. The N-hydroxyphtalimide-catalyzed aerobic oxidation of aldehydes is an environmentally reliable and inexpensive approach for the synthesis of valuable carboxylic acids. However, the reaction may lead to the accumulation of significant amounts of peracid in crude product mixtures thereby generating a considerable safety hazard. Also, in the case of deactivated substrates, long reaction times, high catalyst loading, and stoichiometric additives are required to promote oxidation. Therefore, we developed a flow chemistry-based process for N-hydroxyphtalimide-catalyzed aldehyde oxidations and exploited its benefits to minimize peracid buildup, thereby enhancing the process safety. By performing the aerobic oxidation of aldehydes under continuous flow conditions, chemically intensified and scalable carboxylic acid formation was obtained even in the reactions of deactivated substrates. Our findings are presented herein.

中文翻译：

连续流动条件下N-羟基邻苯二甲酰亚胺催化醛的好氧氧化

合成方法的有效性不仅基于有效的化学物质，还基于放大反应性能和整体安全性的加工策略。N-羟基邻苯二甲酰亚胺催化的醛有氧氧化是合成有价值的羧酸的一种环境可靠且廉价的方法。然而，该反应可能导致在粗产物混合物中积累大量过酸，从而产生相当大的安全隐患。此外，在失活底物的情况下，需要长反应时间、高催化剂负载和化学计量添加剂来促进氧化。因此，我们开发了一种基于流动化学的N-羟基邻苯二甲酰亚胺催化醛氧化，并利用其优势最大限度地减少过酸积聚，从而提高工艺安全性。通过在连续流动条件下进行醛的有氧氧化，即使在失活底物的反应中，也可以获得化学强化和可扩展的羧酸形成。我们的研究结果在此呈现。

更新日期：2022-05-09

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