Synthesis 2012; 44(9): 1405-1409
DOI: 10.1055/s-0031-1290754
paper
© Georg Thieme Verlag Stuttgart · New York

2,6-Bis(phenylethynyl)biphenyls and Their Cyclization to Pyrenes

Mareike M. Machuy
a   Institut für Organische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Gießen, Germany, Fax: +49(641)34309   eMail: prs@org.chemie.uni-giessen.de
,
Christian Würtele
b   Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Gießen, Germany
,
Peter R. Schreiner*
a   Institut für Organische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Gießen, Germany, Fax: +49(641)34309   eMail: prs@org.chemie.uni-giessen.de
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Publikationsverlauf

Received: 12. Februar 2012

Accepted after revision: 17. Februar 2012

Publikationsdatum:
10. April 2012 (online)


Abstract

We present a new protocol for pyrene synthesis via transition-metal cross-couplings. The initially prepared 2,6-bis(phenylethynyl)biphenyls were transformed to pyrenes with uncommon 4,10-disubstitution through an electrophilic cyclization. The precursors were synthesized by Suzuki–Miyaura cross-coupling, which provides 2,6-dibromobiphenyls; these were subsequently coupled with phenylethynyl derivatives via Kumada cross-coupling.