title: Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes.
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.
authors.affiliation: Universitaet Potsdam, Institut fuer Chemie, Organische Synthesechemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany. bernd.schmidt@uni-potsdam.de
authors.forename: Bernd
authors.initials: B
authors.lastname: Schmidt
authors.forename: Nelli
authors.initials: N
authors.lastname: Elizarov
authors.forename: René
authors.initials: R
authors.lastname: Berger
authors.forename: Frank
authors.initials: F
authors.lastname: Hölter
mesh_terms: D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000737:chemistry*; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry; D013343:Styrenes / Q000737:chemistry*
chemical_list: D003979:Diazonium Compounds; D010636:Phenols; D012492:Salts; D013267:Stilbenes; D013343:Styrenes; D010165:Palladium