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.
Author details: | Bernd SchmidtORCiDGND, Nelli Elizarov, René BergerGND, Frank Hölter |
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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): | Keine öffentliche Lizenz: Unter Urheberrechtsschutz |