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Palladium-Catalyzed Double C[BOND]H Activation Directed by Sulfoxides in the Synthesis of Dibenzothiophenes

Authors

  • Dr. Rajarshi Samanta,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany), Fax: (+49) 231-133-2499
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  • Dr. Andrey P. Antonchick

    Corresponding author
    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany), Fax: (+49) 231-133-2499
    • Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany), Fax: (+49) 231-133-2499
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  • We thank Prof. Dr. H. Waldmann for his generous support.

Abstract

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S[DOUBLE BOND]O shows where to go: A novel double C[BOND]H activation of aromatic compounds with a sulfoxide as a directing group results in the highly regioselective synthesis of polysubstituted dibenzothiophenes (see scheme). The reaction cascade consists of palladium-catalyzed double C[BOND]H activation and a Pummerer rearrangement followed by palladium-catalyzed C[BOND]S bond formation.

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