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Synthesis 2013; 45(21): 3038-3043
DOI: 10.1055/s-0033-1339682
paper
© Georg Thieme Verlag Stuttgart · New York

Anti-Friedel–Crafts-Type Substitution To Form Biaryl Linkages

Gergely Gulyas-Fekete
a   Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany   Fax: +49(345)55821309   eMail: bernhard.westermann@ipb-halle.de
b   University of Pécs, Medical School, Department of Biochemistry and Medical Chemistry, Szigeti út 12, 7624 Pécs, Hungary
,
Carlos J. Boluda
a   Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany   Fax: +49(345)55821309   eMail: bernhard.westermann@ipb-halle.de
,
Bernhard Westermann*
a   Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany   Fax: +49(345)55821309   eMail: bernhard.westermann@ipb-halle.de
c   Institute of Organic Chemistry, Martin Luther University Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120 Halle, Germany   eMail: wessjohann@ipb-halle.de
,
Ludger A. Wessjohann*
a   Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany   Fax: +49(345)55821309   eMail: bernhard.westermann@ipb-halle.de
c   Institute of Organic Chemistry, Martin Luther University Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120 Halle, Germany   eMail: wessjohann@ipb-halle.de
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Publikationsverlauf

Received: 19. Juni 2013

Accepted after revision: 08. August 2013

Publikationsdatum:
02. September 2013 (online)

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Abstract

The ipso-substitution of one (or two) hydroxy groups of phloroglucinol with arene nucleophiles (e.g., o-xylene, tetralin, biphenyl) can be achieved easily under Friedel–Crafts-type conditions with or without the use of organic solvents affording a variety of 3,5-dihydroxybiphenyls (57–89% yields). The new method has significant practical advantages compared to classical biaryl-­coupling routes.

Key words

biaryls - dendrimers - arylations - umpolung - Friedel–Crafts

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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