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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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Author:Bernd SchmidtORCiDGND, Nelli Elizarov, René Berger, Frank Hölter
Subtitle (English):a protecting-group economic synthesis of phenolic stilbenes
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (242)
Document Type:Postprint
Date of first Publication:2013/04/09
Year of Completion: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
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer Review:Referiert
Publication Way:Open Access
Licence (German):License LogoKeine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht