BF2-chelated azadipyrromethene (azaBODIPY) is well-known for its prominent near-infrared (NIR) photophysical properties applicable in fields such as biological imaging,labeling,solar concentrators and so on.1 Substituents have been introduced to further red-shift the absorption and emission,however,mainly through pre-functionalizing precursors before the cyclization of pyrroles and the formation of azaBODIPY skeleton,which limits the scope of products.1 Conventional late-stage modifications ofazaBODIPYs,such as Stille and Sonogashira coupling often require tedious multistep synthesis and/or environmentally risky organometallic reagents.2 Herein,a Cu-promoted oxidative direct C-H/C-H coupling reaction is developed as a concise and atom-economic approach to the 2(,6)-arylated azaBODIPYs.The resulted di-indole-azaBODIPY exhibits NIR absorption peak centered at 719 nm with a molar extinction coefficient of 26800 M-1 cm-1.We envision that the newly developed protocol would facilitate the discovery of high performance NIR materials.