Synthesis of N,O-Bidentate Difluoroboron Complexes via Iodide-Promoted Demethylative Borylation

N, O -Bidentate difluoroboron complexes were synthesized from (2-methoxyaryl)pyridines by iodide-promoted demethylative borylation. In the presence of Bu 4 NI and Et 3 N, (2-methoxylaryl)pyridines smoothly reacted with BF 3 ·OEt 2 to afford the N, O -bidentate difluoroboron complexes. The amounts of BF 3 ·OEt 2, Bu 4 NI, and Et 3 N strongly influenced the reaction efficiency. The optimal conditions were determined through Bayesian optimization, and several N, O -bidentate difluoroboron complexes were obtained efficiently under the reaction conditions. The resulting complexes exhibited fluorescent properties with large Stokes shifts, which were in good agreement with the calculated properties.