Transition-Metal-Free Synthesis of C3-Arylated Benzofurans from Benzothiophenes and Phenols

Kevin Yang, Alexander P. Pulis, Gregory J. P. Perry, David J. Procter

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    Abstract

    We report a transition metal-free synthesis of benzofurans from benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Through a sequence involving an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement, phenols can be combined with readily accessible yet synthetically unexplored benzothiophene S-oxides to provide C3- arylated benzofuran products. The products from this approach can undergo subsequent functionalization to gain access to a range of important benzofuran derivatives.
    Original languageEnglish
    Pages (from-to)7498-7503
    JournalOrganic Letters
    Volume20
    Issue number23
    Early online date14 Nov 2018
    DOIs
    Publication statusPublished - 7 Dec 2018

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