Iron-Catalyzed Batch/Continuous Flow C–H Functionalization Module for the Synthesis of Anticancer Peroxides,The Journal of Organic Chemistry

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Iron-Catalyzed Batch/Continuous Flow C–H Functionalization Module for the Synthesis of Anticancer Peroxides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-10 00:00:00 , DOI: 10.1021/acs.joc.7b02854
Moreshwar B. Chaudhari ₁ , Suresh Moorthy ₁ , Sohan Patil ₁ , Girish Singh Bisht ₁ , Haneef Mohamed ₁ , Sudipta Basu ₁ , Boopathy Gnanaprakasam ₁

Affiliation

Iron-catalyzed dehydrogenative cross-coupling of carbonyl compounds with aliphatic peroxide was developed under mild conditions. A library of linear alkylated and arylated peroxides are synthesized in good to excellent yield. This method is highly selective and general for a range of biologically important derivatives of 2-oxindole, barbituric acid, and 4-hydroxy coumarin with a good functional group tolerance and without the cleavage of the peroxide bond. This peroxidation reaction is upscalable to grams and also synthesizable in continuous flow with increased safety in short duration. Mechanistic investigation reveals Fe-(II) undergoes redox type process to generate the radical intermediates, which subsequently recombine selectively to form the stable peroxides. The potential of peroxides is evaluated by cell viability assay and found to exhibit the good anticancer activity with minimum IC₅₀= 5.3 μM.

中文翻译：

铁催化的分批/连续流C–H功能化模块，用于合成抗癌过氧化物

在温和条件下开发了铁催化的羰基化合物与脂肪族过氧化物的脱氢交叉偶联反应。合成直链烷基化和芳基化的过氧化物的库具有良好至极好的收率。该方法对2-氧吲哚，巴比妥酸和4-羟基香豆素具有重要的官能团耐受性且没有过氧化物键的裂解的生物学上重要的一系列衍生物具有高度的选择性和通用性。该过氧化反应可升级至克级，并且还可以在连续流中合成，并且在短时间内提高了安全性。机理研究表明，Fe-（II）经历了氧化还原型过程以生成自由基中间体，该中间体随后选择性地重组以形成稳定的过氧化物。₅₀ = 5.3μM。

更新日期：2018-01-10

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