Lithiation of palladated dihydropentacene: a new route for the introduction of substituents from both of electrophiles and nucleophiles to pentacene

Dibromodihydropentacene compound 1 was palladated and then lithiated to give a lithiated-palladated intermediate. Both of the lithium moiety and the palladium complex moiety on dihydropentacene unexpectedly survived in the solution. The Li and Pd moieties reacted with electrophiles and nucleophiles respectively to give the substituted dihydropentacene products. Aromatization of these dihydropentacenes gave substituted pentacene derivatives.