Regioselective synthesis of C3 alkylated and arylated benzothiophenes

Harry Shrives, Jose A. Fernandez-Salas, Christin Hedtke, Alexander Pulis, David Procter

    Research output: Contribution to journalArticlepeer-review


    Benzothiophenes are heterocyclic constituents of important molecules relevant to society, including those with the potential to meet modern medical challenges. The construction of molecules would be vastly more efficient if carbon–hydrogen bonds, found in all organic molecules, can be directly converted into carbon–carbon bonds. In the case of elaborating benzothiophenes, functionalization of carbon–hydrogen bonds at carbon-number 3 (C3) is markedly more demanding than at C2 due to issues of regioselectivity (C3 versus C2), and the requirement of high temperatures, precious metals and the installation of superfluous directing groups. Herein, we demonstrate that synthetically unexplored but readily accessible benzothiophene S-oxides serve as novel precursors for C3-functionalized benzothiophenes. Employing an interrupted Pummerer reaction to capture and then deliver phenol and silane coupling partners, we have discovered a directing group-free method that delivers C3-arylated and -alkylated benzothiophenes with complete regioselectivity, under metal-free and mild conditions.
    Original languageEnglish
    Article number14801
    Number of pages7
    JournalNature Communications
    Early online date20 Mar 2017
    Publication statusPublished - 2017


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