Activation of Meso ‐AmidoBODIPYs for Mild Pd‐Catalyzed Cross‐Coupling With Boronic Acids

A mild and operationally simple method for the synthesis of meso ‐arylBODIPYs enabled by a geometrically activated bis‐acetamidoBODIPY is described. The new meso ‐bis‐acetamidoBODIPY enables Suzuki–Miyaura cross‐coupling at room temperature with a variety of arylboronic acids, affording a family of 17 meso ‐arylBODIPYs in moderate to good yields (20%–90%) within short reaction times. Computational studies revealed that the bis‐acetamidoBODIPY exhibits the longest N─C8 bond and a large distortion angle (89.7°), approaching full orthogonality. These structural features explain its use as an activated platform for meso ‐functionalization through Suzuki–Miyaura cross‐coupling. The optical properties of the meso ‐bis‐acetamidoBODIPY were evaluated, highlighting the role of the meso ‐substituent nature and its geometric arrangement on the photophysical properties compared with the previously reported 8‐aminoBODIPY and 8‐acetamidoBODIPY analogs.