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Scope and limitations of the Heck–Matsuda-coupling of phenol diazonium salts and styrenes

  • 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.

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Metadaten
Author details:Bernd SchmidtORCiDGND, Nelli Elizarov, René BergerGND, Frank Hölter
URN:urn:nbn:de:kobv:517-opus4-95070
Subtitle (English):a protecting-group economic synthesis of phenolic stilbenes
Publication series (Volume number):Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (242)
Publication type:Postprint
Language:English
Date of first publication:2013/04/09
Publication year:2013
Publishing institution:Universität Potsdam
Release date:2016/09/06
Tag:arenediazonium salts; arylboronic acids; aryldiazonium salts; boronic acid; catalyzed cross metathesis; o bond formation; palladium catalyst; stereoselective-synthesis; substituted stilbenes; trans-stilbenes
First page:3674
Last Page:3691
Source:Org. Biomol. Chem. (2013) Nr. 11, S. 3674-3691. - DOI: 10.1039/C3OB40420J
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
Publishing method:Open Access
License (German):License LogoKeine öffentliche Lizenz: Unter Urheberrechtsschutz
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