Abstract : A new route to 1,3-diarylisobenzofurans was developed with the goal to obtain new polyaromatic N-hydroxyimides. It involves the chemoselective addition of aryl magnesium reagents or aryl boronic acids to the aldehyde function of o-aroylbenzaldehydes, themselves obtained by a versatile Kotali reaction. This original method allowed the synthesis of various functionalized 1,3-diarylisobenzofurans and it was applied to the synthesis of 17 new polyaromatic N-hydroxyimides. Diversification reactions without protection of the N hydroxyimide function were successfully performed on these compounds. The biological activity of these compounds was evaluated and allowed the characterization of a new class of Protein Kinase CK2 inhibitors. In addition the synthesized compounds showed a good activity as aerobic oxidation catalysts. All products presented higher activity than NHPI and one of them showed catalytic properties similar to NHTTPI.