This study describes the synthesis of an acridone through the directed lithiation of a diarylamine, and elaboration via the 4,5-dibromoacridone. The bromo substituents are amenable to Suzuki-Miyaura coupling. Conversion to a 9chloro-4,5-dibromoacridine, followed by bromine-lithium ex-change, allows the preparation of a 4,5-bis (phosphino)-9chloroacridine. The 9-chloro moiety undergoes nucleophilic aromatic substitution by methoxide or an aryloxide. Oneelectron reduction of a 9-(aryloxy)-4,5-bis(phosphino)acridine affords a stable radical anion.
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