4.4 Article

Direct C-H Arylation of Quinones with Anilines

Journal

SYNLETT
Volume -, Issue 11, Pages 1621-1624

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1291163

Keywords

quinone; aryl diazonium salt; aniline; direct C-H arylation; radical

Funding

  1. 'Ligue Contre Le Cancer', the 'Agence Nationale de la Recherche' [ANR JCJC 7141]
  2. Association pour la Recherche sur le Cancer (ARC)
  3. Region Aquitaine
  4. Centre National de Recherche Scientifique (CNRS)

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We discovered that anilines were suitable for the direct C-H arylation of benzoquinone in the presence of tert-butyl nitrite. This new reaction proceeds through the in situ formation of a diazonium hydroxide species. The coupling can be carried out at room temperature under neutral, additive-free, metal-free, and aqueous conditions, allowing an environmentally friendly procedure.

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