3 years ago
Iron-Catalyzed Batch/Continuous Flow C–H Functionalization Module for the Synthesis of Anticancer Peroxides
Girish Singh Bisht, Moreshwar B. Chaudhari, Suresh Moorthy, Haneef Mohamed, Boopathy Gnanaprakasam, Sudipta Basu, Sohan Patil
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.
Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02854
DOI: 10.1021/acs.joc.7b02854
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