Arylation of Phenols. Convenient, Regiospecific Methods for Mono- or Bis-p-fluorophenylations, Suitable for Large Scale Syntheses

Article abstract of DOI:10.1055/s-1990-27028

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.