Synthesis of helicenes and related compounds

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Metal-catalyzed reactions of alpha-functionalized biphenyls with acetylenes and nitriles lead to phenanthrenes and nitriles, respectively. This well-known transformations shall be extended to functionalized acetylenes and nitriles to finally yield perylene quinones, benzo[de]anthracenes and benzoacridines. Starting with suitably substituted and thus chiral biphenyls would lead to enantiomerically pure, axially chiral perylene quinones. In expansion of this strategy, the reaction of oligo-ortho-phenylenes with acetylenes or nitriles would furnish helicenes and aza-helicenes, respectively. With this, the synthesis of substituted helicenes could be achieved. Since oligophenylenes are available in enantiomerically pure form, the enantioselective synthesis of helicenes is possible. Multiple Friedel-Crafts acylation of oligophenylenes with carboxyl chloride functions in the alpha positions would yield new helicene analogues with keto functions in the periphery, which could be further transformed and functionalized. Interesting physical properties can be expected for these compounds