Synthesis and Reactivity of 3,5-Diiodo-BODIPYs via a Concerted, Double Aromatic Finkelstein Reaction

3,5-Diiodo-8-aryl-BODIPYs are prepared from the corresponding 3,5-dichloro- and 3,5-dibromo- congeners via a double aromatic Finkelstein reaction with NaI in refluxing propionitrile, in yields from 51 to 100%. Rate enhancement is observed for 3,5-dibromo-BODIPYs (ArBr > ArCl) suggesting a concerted S_NAr mechanism for this transformation. Thus formed 3,5-diiodo-BODIPYs are examined as coupling partners in Migita–Kosugi–Stille, Mizoroki–Heck, Sonogashira, and Suzuki–Miyaura reactions, providing routes toward complex BODIPY architectures.