Convergent and Functional-Group-Tolerant Synthesis of B-Organo BODIPYs.

Boron-dipyrromethenes (BODIPYs) are one of the most important fluorescent materials. Despite their potential unique properties, however, B,B-fluoro-organo BODIPYs (BFR-BODIPYs) possessing an organo group (R) on the boron center have not been studied in detail, due in part to challenges related to their synthesis. In this paper, a convergent synthesis of BFR-BODIPYs operative under mild conditions is reported. Conversions of the thus-synthesized functionalized BFR-BODIPYs by cross-coupling, condensation, and SN2 reactions at the R group are also demonstrated.