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Electrochemical Oxidation of Alcohols and Aldehydes to Carboxylic Acids Catalyzed by 4-Acetamido-TEMPO: An Alternative to “Anelli” and “Pinnick” Oxidations
ACS Catalysis ( IF 12.9 ) Pub Date : 2018-06-11 00:00:00 , DOI: 10.1021/acscatal.8b01640
Mohammad Rafiee 1 , Zachary M. Konz 1 , Matthew D. Graaf 2 , Hannes F. Koolman 3 , Shannon S. Stahl 1
Affiliation  

An electrocatalytic method has been developed to oxidize primary alcohols and aldehydes to the corresponding carboxylic acids using 4-acetamido-2,2,6,6-tetramethylpiperidin-1-oxyl (ACT) as a mediator. The method successfully converts benzylic, aliphatic, heterocyclic, and other heteroatom-containing substrates to the corresponding carboxylic acids in aqueous solution at room temperature. The mild conditions enable retention of stereochemistry adjacent to the site of oxidation, as demonstrated in a 40 g-scale synthesis of a precursor to levetiracetam, a medication used to treat epilepsy.

中文翻译:

4-乙酰胺基-TEMPO催化醇和醛电化学氧化成羧酸:“ Anelli”和“ Pinnick”氧化的替代方法

已经开发出一种电催化方法,使用4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧基(ACT)作为介体,将伯醇和醛氧化为相应的羧酸。该方法在室温下将水溶液中的苄基,脂族,杂环和其他含杂原子的底物成功转化为相应的羧酸。温和的条件能够使立体化学保留在氧化位点附近,如左乙拉西坦(一种用于治疗癫痫的药物)的前体的40克规模合成所证明的。
更新日期:2018-06-11
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