Polycyclic aromatic hydrocarbons (PAHs) are composed of linked aromatic rings, used as building blocks in the construction of larger molecules. One method of constructing PAHs is indenoannulation, involving an intramolecular cyclization that produces a 5-membered ring between a benzene ring and a base PAH. There are various methods that are used to produce indenoannulated products, however, each method has disadvantages restricting their use in synthesizing large PAH compounds. Our proposed method uses a Buchwald-Hartwig cross coupling reaction in order to install cyclohexanone units onto a base PAH, followed by the conversion of the product to a regiospecific enol-triflate. The final step of our proposed method uses a palladium-catalyzed cyclization reaction closing the 5-membered ring. With our new method we hope to synthesize larger PAHs compounds such as tetraindenopyrene and then study their unique photophysical properties with prospective applications in organic electronics and solar cells.

Palladium-catalyzed indenoannulations

245th National Meeting (2013)

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