Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes

Org Biomol Chem. 2013 Jun 14;11(22):3674-91. doi: 10.1039/c3ob40420j.

Abstract

4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4'-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior.

MeSH terms

  • Catalysis
  • Diazonium Compounds / chemistry*
  • Palladium / chemistry
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Salts / chemistry*
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry
  • Styrenes / chemistry*

Substances

  • Diazonium Compounds
  • Phenols
  • Salts
  • Stilbenes
  • Styrenes
  • Palladium