Build-Up of Double Carbohelicenes Using Nitroarenes: Dual Role of the Nitro Functionality as Activation and Leaving Group
The construction of double carbohelicenes is a 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 including 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 conventional coupling reaction. In this work, the palladium-catalyzed Heck-type alkenylation of nitroarenes has been presented, in which the conventionally inert Ar−NO2 bond is cleaved. This work provides a novel synthetic strategy for polycyclic aromatic hydrocarbons (PAHs).