Fluoride-induced cyclization of pentacenequinone to higher quinones.

Novel pentacenequinone derivatives 3, 7, and 10 have been synthesized via Suzuki-Miyaura coupling. Derivatives 3 and 7 having OTBS groups undergo irreversible fluoride-induced cyclization to substituted higher quinones in the presence of TBAF in dry THF using one-pot, two-step strategies in moderate yields. These functionalized higher quinone derivatives are freely soluble in THF and DMSO and can be used as precursors for the synthesis of higher acene derivatives.