4.8 Article

Cross Dehydrogenative Coupling via Base-Promoted Homolytic Aromatic Substitution (BHAS): Synthesis of Fluorenones and Xanthones

Journal

ORGANIC LETTERS
Volume 15, Issue 4, Pages 928-931

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol4000857

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Funding

  1. program Sustainable Chemical Synthesis (SusChemSys)
  2. European Regional Development Fund (ERDF)
  3. state of North Rhine-Westphalia, Germany

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Cross dehydrogenative coupling reactions occurring via base-promoted homolytic aromatic substitutions (BHASs) are reported. Fluorenones and xanthones are readily prepared via CDC starting with readily available ortho-formyl biphenyls and ortho-formyl biphenylethers, respectively. The commercially available and cheap tBuOOH is used as an oxidant. Initiation of the radical chain reaction Is best achieved with small amounts of FeCp2 (0.1 or 1 mol %).

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