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The construction of double carbohelicenes is highly fascinating yet challenging work. Disclosed herein is a streamlined and simplified synthetic route to double carbohelicenes starting from nitroarenes through sequential nitro-activated ortho -C-H arylation, denitrative alkenylation and intramolecular cyclodehydrogenation. In this synthetic strategy, the nitro group plays a dual role namely as a leaving group for the denitrative alkenylation and as an activating group for ortho -C-H arylation, which is distinct from those of aryl halides in a conventional coupling reaction. In this work, the palladium-catalyzed Heck-type alkenylation of nitroarenes has been presented, in which the conventionally inert Ar-NO 2 bond is cleaved. This work provides a novel synthetic strategy for polycyclic aromatic hydrocarbons (PAHs).

Build-up of double carbohelicenes using nitroarenes: dual role of the nitro functionality as an activating and leaving group