Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines

Abstract

AbstractThe construction of C−N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as a green oxidant. By this strategy, a series of weak nitrogen nucleophiles, such as heteroaryl and aryl anilines, were installed to the α‐position. Remarkably, pyrrole, pyrazole and indole were also employed to realize the synthesis of α‐heteroaryl BODIPYs through direct functionalization. Further aggregation‐induced emission enhancement (AIE) properties and lipid droplet‐targeting bioimaging experiments of representative dyes demonstrated their potential applications as organic probes.