Novel Synthesis of α-Keto Esters and Amides by an sp3 C–H Oxidation of Nitromethyl Aryl Ketones Promoted by Ion-Supported (Diacetoxyiodo)benzene

A simple and efficient method is described for the preparation of α-keto esters or amides from nitromethyl aryl ketones. In the presence of nucleophiles (alcohols or amines), the ion-supported (di­acetoxyiodo)benzene-promoted sp3 C–H oxidation of nitromethyl aryl ketones proceeded efficiently under mild conditions to give the corresponding α-keto esters and amides in moderate to good yields. This is the first reported use of (diacetoxyiodo)benzene in the synthesis of α-keto esters and amides. The reaction is ecofriendly and has the ­advantages of mild conditions, short reaction times, and a recyclable reagent.

本研究报道了一种以硝基甲基芳基酮为原料制备α-酮酯或α-酮酰胺的简便高效方法。在亲核试剂（醇类或胺类）存在下，离子负载型二乙酰氧基碘苯（(diacetoxyiodo)benzene）介导的硝基甲基芳基酮sp³碳氢键氧化反应可在温和条件下高效进行，以中等至优异的收率得到相应的α-酮酯与α-酮酰胺。本研究首次报道将二乙酰氧基碘苯用于α-酮酯及α-酮酰胺的合成。该反应具有环境友好的特点，同时具备反应条件温和、反应时长较短、试剂可回收利用等优势。