Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals

Sara Morcillo, Elizabeth Dauncey, Ji Hye Kim, James J. Douglas, Nadeem S Sheikh, Daniele Leonori

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    Abstract

    The selective functionalization of C(sp3)−H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late‐stage functionalization of amino acids and a dipeptide.
    Original languageEnglish
    Pages (from-to)12945-12949
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume57
    Issue number39
    Early online date3 Aug 2018
    DOIs
    Publication statusPublished - 19 Sept 2018

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