Issue 22, 2013

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Feb 2013
Accepted
08 Apr 2013
First published
09 Apr 2013

Org. Biomol. Chem., 2013,11, 3674-3691

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

B. Schmidt, N. Elizarov, R. Berger and F. Hölter, Org. Biomol. Chem., 2013, 11, 3674 DOI: 10.1039/C3OB40420J

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