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Issue 22, 2013
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Scope and limitations of the Heck–Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes

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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

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Publication details

The article was received on 28 Feb 2013, accepted on 08 Apr 2013 and first published on 09 Apr 2013


Article type: Paper
DOI: 10.1039/C3OB40420J
Citation: Org. Biomol. Chem., 2013,11, 3674-3691

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    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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