Photoredox Synthesis of Aryl-Hydroxylamines from Carboxylic Acids and Nitrosoarenes

Jacob Davies, Lucrezia Angelini, Mohammed A Alkhalifah, Laia Malet Sanz, Nadeem S Sheikh, Daniele Leonori

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    Abstract

    Hydroxylamines are found in biologically active compounds and serve as building blocks for the preparation of nitrogen-containing molecules. Here, we demonstrate the direct conversion of carboxylic acids into the corresponding alkyl hydroxylamines using organo-photoredox catalysis. The process relies in the generation of alkyl radicals via photo-induced oxidation–decarboxylation and their following reaction with nitrosoarenes. We have successfully applied this method to the late-stage modification of complex and biologically active acids and applied it in novel radical cascade processes.
    Original languageEnglish
    JournalSynthesis
    Early online date2 Jan 2018
    DOIs
    Publication statusPublished - 2018

    Keywords

    • hydroxylamines
    • radical addition
    • nitrosoarenes
    • late-stage functionalization
    • radical cascade
    • photoredox

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