Controlling theSymmetry of Perylene Derivatives viaSelective <i>ortho</i>-Borylation

This work presents a systematic and rational approach to the synthesis of previously reported as well as novel tetra- and di-<i>ortho</i>-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 <i>ortho</i>-functionalization of perylene derivatives.