Enantioselective Synthesis of Polysubstituted Boron-Stereogenic BODIPYs Enabled by Pd/Norbornene Catalysis
Abstract
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.
Fields of Study & Subjects
Luminescence and Fluorescent Materials
Organoboron and organosilicon chemistry
Supramolecular Chemistry and Complexes
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 24
- Pages
- 25258–25268
- Publication date
- 11 June 2026
- Language
- EN