In this work a synthetic protocol was developed to obtain a series of diarylborinic complexes bearing a diarylboron moiety chelated with various bidentate N,O-ligands derived from 5-chloro-8-hydroxy-7-iodoquinoline, quinoline-2,4-dicarboxylic acid or 2-(2-hydroxy-5-methylphenyl)benzotriazole. The obtained complexes were characterized by NMR, IR, CV, UV–vis and single-crystal X–ray diffraction analyses. The experimental data were supported by theoretical calculations. The obtained complexes were tested as singlet oxygen sensitizers for the oxidation of 2-furancarboxylic acid, oxidative coupling of benzylamines and oxidation of sulfides. Among the studied compounds, the diarylborinic derivative bearing a 5-chloro-8-oxy-7-iodoquinolinate ligand was selected as the most economic singlet oxygen sensitizer. However, the diphenylborinic complex bearing an 8-oxyquinolinate ligand was the most efficient for the selective oxidation of various benzylamines to their respective N-benzylidene benzylamines.