The reaction of [Zr(biphe)3][(Li.(THF)4)2], where biphe is 2,2'-biphenyldiyl, with an o-dihaloarene produces a triphenylene. Two new bonds are created in this rare example of an uncatalyzed, Zr-mediated aryl-aryl bond formation. Multiple biphe fragments can be incorporated to give larger triphenylene-containing polycyclic aromatic hydrocarbons. This reaction can introduce significant strain and was demonstrated to tolerate alkyl and methoxy substituents.
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Hilton et al. (2006) studied this question.
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