[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.
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Iglesias et al. (2004) studied this question.
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