Enantioselective Pd0-Catalyzed C(sp2)-H Arylation for the Synthesis of Chiral Warped Molecules

C-H activation-based ring-forming methods are a powerful approach for the construction of complex molecular architectures, especially those containing a congested stereocenter. Therefore, this strategy seems perfectly suited to address the synthesis of chiral polycyclic aromatic hydrocarbons (PAHs) and bowl-shaped molecules, which are important target molecules in the field of organic electronic materials. Herein, we describe an enantioselective Pd0-catalyzed C(sp2)-H arylation protocol for the synthesis of chiral fluoradenes and other warped molecules, which could serve to the bottom-up construction of chiral PAHs. The current approach relies on the use of chiral bifunctional phosphine-carboxylate ligands and delivers diverse polycyclic compounds in high yield and with good to excellent enantioselectivity. The chiroptical properties of the obtained products were investigated, and some of them were found to have a strong ellipticity and an emission band located in the visible region.