Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization

Authors

  • Eva Koch,

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

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster (Germany)
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster (Germany)
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  • We thank the Fonds der Chemischen Industrie for support (stipend to E. K.).

Abstract

original image

Ipso, meta, and para: Benzoic acid derivatives can be highly regioselectively substituted at the ipso, meta, and para positions. The reaction sequence comprises an alkylative Birch reduction, a 4-alkylation, a palladium-catalyzed γ-arylation, and an oxidative rearomatization (see scheme). All the reactions are robust and experimentally easy to conduct.

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