Accessible azaacenes: Pd-catalyzed coupling reactions between aromatic diamines and unactivated aromatic dibromides furnish N,N′-dihydrodiazapentacenes, -hexacenes, and -heptacenes (see scheme; TIPS=triisopropylsilyl). Oxidation of these products led to diazapentacenes and a diazahexacene. The existence of a diazaheptacene intermediate was proven by solving the single-crystal structure of its (4+4) dimerization product.
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Engelhart et al. (2013) studied this question.
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