Tris(benzocyclobutadieno)triphenylene and Its Lower Biphenylene Homologues by Palladium-Catalyzed Cyclizations of 2,3-Didehydrobiphenylene
- 31 August 2004
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (20) , 3557-3560
- https://doi.org/10.1021/ol048548o
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.Keywords
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