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Reactions of Arynes with Nitrosoarenes—An Approach to Substituted Carbazoles

Authors

  • Shyamal Chakrabarty,

    1. NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster (Germany)
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  • Dr. Indranil Chatterjee,

    1. NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster (Germany)
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  • Dr. Ludger Tebben,

    1. NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster (Germany)
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  • Prof. Dr. Armido Studer

    Corresponding author
    1. NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster (Germany)
    • NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster (Germany)
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  • We thank the DFG for supporting our work.

Abstract

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No transition metals are necessary in the reaction of in situ generated arynes with nitrosoarenes to give substituted carbazoles. Depending on the fluoride source and the solvent, either N-arylated carbazoles or NH-carbazoles are obtained (see scheme; DME=dimethoxyethane, OTf=trifluoromethanesulfonate). In these cascades a C[BOND]C and one or two C[BOND]N bonds are formed. The reactions are easy to conduct and proceed under mild conditions.

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