Enantioselective Synthesis of Polysubstituted Boron-Stereogenic BODIPYs Enabled by Pd/Norbornene Catalysis

Boron-stereogenic BODIPYs represent an emerging class of chiral fluorophores with promising applications in materials science and bioimaging; however, their enantioselective synthesis, particularly for multiply substituted variants, remains highly challenging. Herein, we report an enantioselective Catellani desymmetrization strategy that enables efficient access to structurally complex boron-stereogenic BODIPYs. The reaction delivers a broad range of products (87 examples) with excellent enantioselectivity (up to 99% ee) and high chemoselectivity. The method tolerates diverse functional groups and provides versatile scaffolds for further derivatization without a loss of enantiopurity. Moreover, the resulting BODIPYs exhibit tunable photophysical properties and efficient cellular uptake, highlighting their potential use in optoelectronic and bioimaging applications.