Academy of Scientific and Innovative Research, CSIR-Human Resource Development Centre (CSIR-HRDC), Campus, Sector 19, Kamla Nehru Nagar, Ghaziabad, Uttar Pradesh 201002, India.
Org Lett. 2020 Dec 4;22(23):9381-9385. doi: 10.1021/acs.orglett.0c03666. Epub 2020 Nov 18.
The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford -aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical from water to produce amide. Mechanistic insight allowed the scope of the strategy to be expanded to the synthesis of amides via reaction between aryl α-ketocarboxylic acids and nitroso compounds.
描述了在氧化水相条件下，用 5-芳基-3-硝基异恶唑-4-羧酸酯和取代的二硝基苯将芳基α-酮羧酸进行脱羧/氧化酰胺化反应，得到芳基酰胺。该反应被认为是通过自由基途径进行的，其中苯甲酰基氮氧自由基是由硝基芳烃与乙二醛自由基反应形成的关键中间体，与水中的羟基自由基结合生成酰胺。通过机理研究，该策略的适用范围扩大到通过芳基α-酮羧酸和亚硝基化合物之间的反应合成酰胺。
