Dialling-In New Reactivity into the Shono-Type Anodic Oxidation Reaction,The Chemical Record

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Dialling-In New Reactivity into the Shono-Type Anodic Oxidation Reaction
The Chemical Record ( IF 7.0 ) Pub Date : 2020-11-04 , DOI: 10.1002/tcr.202000116
Alan M Jones ₁

Affiliation

This Personal Account describes the author's groups’ research in the field of electrosynthetic anodic oxidation, beginning with initial trial and error attempts with the Shono oxidation. Early setbacks with complex rotameric amide mixtures, provided the ideal environment for the discovery of the Oxa-Shono reaction-O_sp²-C_sp³ bond cleavage of esters-providing two useful products in one-step: aldehyde selective oxidation level products and a mild de-esterification method to afford carboxylic acids in the process. The development of the Oxa-Shono reaction provided the impetus for the discovery of other electrically propelled-N_sp²-C_sp² and N_sp²-C_sp³-bond breaking reactions in bioactive amide and sulfonamide systems. Understanding the voltammetric behaviour of the molecule under study, switching between controlled current- or controlled potential- electrolysis, and restricting electron flow (the reagent), affords exquisite control over the reaction outcomes in batch and flow. Importantly, this bio-inspired advance in electrosynthetic dealkylation chemistry mimics the metabolic outcomes observed in nature.

中文翻译：

在 Shono 型阳极氧化反应中拨入新的反应性

此个人帐户描述了作者小组在电合成阳极氧化领域的研究，从 Shono 氧化的初步试验和错误尝试开始。复杂旋转异构酰胺混合物的早期挫折为发现 Oxa-Shono 反应-酯的O _sp² - C _sp³键断裂提供了理想的环境-一步提供两种有用的产物：醛选择性氧化水平产物和在此过程中采用温和的脱酯化方法得到羧酸。Oxa-Shono 反应的发展为发现其他电力驱动的N _sp² - C _sp提供了动力²和N _sp² - C _sp³ -生物活性酰胺和磺胺系统中的键断裂反应。了解所研究分子的伏安行为、在受控电流或受控电势电解之间切换以及限制电子流（试剂），可以精确控制批次和流量中的反应结果。重要的是，这种电合成脱烷基化学方面的生物启发性进展模拟了自然界中观察到的代谢结果。

更新日期：2020-11-04

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