Construction of axial chirality via palladium/chiral norbornene cooperative catalysis

Axially chiral biaryls are common structural motifs in functional materials, bioactive natural products, pharmaceuticals and chiral catalysts/ligands. As such, efficient preparation of these privileged scaffolds is an important endeavour in organic chemistry. Herein we report a general and modular platform technology for the construction of axial chirality via palladium/chiral norbornene cooperative catalysis. It is a three-component cascade process that involves widely available aryl iodides, 2,6-substituted aryl bromides and olefins (or alkynes, boronic acids and so on) as the reactants. A wide variety of substrates bearing an assortment of functional groups (88 examples) are compatible with this method. Other features include a distinct stereoinduction model, excellent enantioselectivities, step economy and scalability. This method is also amenable for the synthesis of chiral fluorenols through axial-to-central chirality transfer in high stereochemical fidelity. We anticipate that this work will have broad synthetic utilities in chiral ligands and catalyst-design for asymmetric catalysis.