Palladium-Catalyzed Tandem C-C Activation/Cyclization Induced by Carbopalladation of Functionalized Nitriles: Synthesis of Benzo Dipyrromethenes.

A palladium-catalyzed carbon-carbon bond activation-initiated reaction of 2-(3-phenyloxiran-2-yl)benzonitriles with arylboronic acids is reported. Multiple chemical bonds were cleavaged and reconstructed via β-carbon elimination in this reaction, enabling the construction of valuable benzo-fused dipyrromethenes that are difficult to prepare by other methods. Additionally, a series of benzannulated boron dipyrromethenes are synthesized and show practical significance in terms of expanding the applications and types of fluorescent materials. The proposed mechanism is supported by preliminary mechanistic experiments.