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Synthesis 1990; 1990(9): 827-833
DOI: 10.1055/s-1990-27028
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Arylation of Phenols. Convenient, Regiospecific Methods for Mono- or Bis-p-fluorophenylations, Suitable for Large Scale Syntheses

Heiner Jendralla* , Li-Jian Chen
  • *Hoechst AG, Postfach 800320, D-6230 Frankfurt/Main 80, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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Phenols have been arylated by a palladium(0)-catalyzed coupling reaction. Two methods were used: a Grignard reagent of a protected phenol component 2 was coupled with a haloarene, or an umpolung (reversed reactivity) where unprotected phenolic halides 6 were coupled with aryl Grignard reagents. Bis-arylation and regiospecific ortho-, meta- and para-arylations were achieved. Aryl-aryl couplings were insensitive to steric hindrance in the Grignard component, but were inhibited by sulfur-containing substituents in the phenolic component. A thiocyanate substituted biaryl was used to synthesize arylated phenols with various sulfur functionalities.