Palladium-catalyzed direct C-H arylations of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) with 3,4-ethylenedioxythiophene (EDOT) derivatives at relatively low temperature (60 °C) provide moderate to good yields (47%-72%) of products having potential applications in fluorescent bioimaging and organic optoelectronics.