Tris(benzocyclobutadieno)triphenylene and its lower biphenylene homologues by palladium-catalyzed cyclizations of 2,3-didehydrobiphenylene

Organic Letters
Beatriz IglesiasK Peter C Vollhardt

Abstract

[reaction: see text] The Pd-catalyzed cycloaddition of didehydrobiphenylenes 2a,b, generated from the corresponding 3-(trimethylsilyl)-2-biphenylenyl triflates with fluoride, furnishes the C3-symmetric trimers 1a,b in which the embedded triphenylene unit is distorted to increase the aromaticity of the central benzene ring. Cocyclization of 2a,b with dimethyl acetylenedicarboxylate provides the phenanthrene- and naphthalenecarboxylic ester analogues, depending on the catalyst used.

References

Apr 1, 1986·Journal of the American Chemical Society·M Hirthammer, K P Vollhardt
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Mar 15, 1999·Angewandte Chemie·Christian EickmeierK Peter C Vollhardt

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Citations

Aug 27, 2009·Chemical Communications : Chem Comm·Toshihiko Iwayama, Yoshihiro Sato
Oct 20, 2010·Chemical Communications : Chem Comm·Alastair A CantMichael F Greaney
Apr 28, 2017·Chemical Communications : Chem Comm·Yingjie MaKlaus Müllen
Apr 13, 2018·Physical Chemistry Chemical Physics : PCCP·Szymon GodlewskiDolores Pérez
Sep 30, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Slavko RadenkovićPatrick Bultinck
Jun 24, 2006·Chemistry : a European Journal·Carmen RomeroEnrique Guitián
Jan 27, 2019·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Changding GuoXia Zuo
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Jul 13, 2006·The Journal of Physical Chemistry. a·Jerome M Schulman, Raymond L Disch
Sep 18, 2008·The Journal of Organic Chemistry·Carmen RomeroEnrique Guitián
Jul 28, 2011·Organic Letters·Grégory PietersDamien Prim
Sep 14, 2007·The Journal of Physical Chemistry. a·Jerome M Schulman, Raymond L Disch
Apr 23, 2005·The Journal of Organic Chemistry·Man-kit LeungBih-Yaw Jin

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