Alkene Carboarylation via Catalyst‐Free, Visible Light‐Mediated Smiles Rearrangement.

David Whalley, Hung Duong, Michael Greaney

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    A light‐mediated Truce–Smiles arylative rearrangement is described that proceeds in the absence of any photocatalyst. The protocol creates two C−C bonds from simple starting materials, with the installation of an aryl ring and a difluoroacetate moiety across unactivated alkenes. The reaction proceeds via a radical mechanism, utilizing a light‐mediated reduction of ethyl bromodifluoroacetate by N,N,N′,N′‐tetramethylethylenediamine (TMEDA) to set up intermolecular addition to an unactivated alkene, followed by Truce–Smiles rearrangement.
    Original languageEnglish
    Pages (from-to)1927-1930
    JournalChemistry – A European Journal
    Early online date7 Dec 2018
    Publication statusPublished - 2019


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