[3+2+1] Pyridine Skeleton Synthesis Using Acetonitrile as C4N1 Units and Solvent

The first [3 + 2 + 1] methodology for pyridine skeleton synthesis via cascade carbopalladation/cyclization of acetonitrile, arylboronic acids, and aldehydes was developed. This reaction proceeds via six step tandem reaction sequences involving the carbopalladation reaction of acetonitrile, a nucleophilic addition, a condensation, an intramolecular Michael addition, cyclization, and aromatization. Delightfully, both palladium acetate and supported palladium nanoparticles catalyzed this reaction with similar catalytic performance. The characterization results of the fresh and used supported palladium nanoparticle catalysts indicated that the reaction might be performed via a Pd(0)/Pd(II) catalytic cycle that began with Pd(0). Furthermore, the products showed good fluorescence characteristics. The green homogeneous/heterogenous catalytic methodologies pave a new way for constructing the pyridine skeleton.

Automated summary

A novel methodology was developed for the synthesis of pyridine skeleton through cascade reaction of acetonitrile, arylboronic acids, and aldehydes. Both palladium acetate and supported palladium nanoparticles showed similar catalytic performance in this reaction, suggesting a possible Pd(0)/Pd(II) catalytic cycle. The products exhibited good fluorescence characteristics, indicating a promising approach for constructing pyridine skeleton.