NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs
Yuan‐Yuan Gao, Yu-Jing Liang, Gao‐Wei Li, Li Lu, Zhiyuan Hu, Wenhao Lin, Xuehui Huang, Yu Chen, Xuzhao Du, Peiyuan Yu, Qiuling Song, Lantao Liu
Abstract
The enantioselective synthesis of boron-stereogenic compounds remains a formidable challenge in modern synthetic chemistry due to the limited availability of efficient catalytic strategies. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed kinetic resolution of 3-formyl BODIPYs, which provides access to enantioenriched 3-formyl BODIPYs and aryl 3-carboxylate BODIPYs in good to high yields with high enantioselectivities (up to 96% ee). This method features a broad substrate scope, mild reaction conditions, and exceptional functional group tolerance. Furthermore, the resulting chiral BODIPYs exhibit promising circularly polarized luminescence properties. This work represents the successful application of NHC catalysis for constructing boron-stereogenic centers, expanding the toolbox for asymmetric organocatalysis.