Controlling the Symmetry of Perylene Derivatives via Selective ortho-Borylation

This work presents a systematic and rational approach to the synthesis of previously reported as well as novel tetra- and di-ortho-borylated perylene, perylenediimide, and perylenemonoimide scaffolds. Through optimization of the reaction conditions, employing [Ir­(OMe)­(COD)]2 as a catalyst and suitable ligands, efficient tetraborylation and regioselective diborylations were achieved. Additionally, the reaction times were reduced from days to hours under microwave irradiation, rendering this methodology a practical and scalable route for the ortho-functionalization of perylene derivatives.