Abstract
Background: The N-aryl piperazines are an important component of many drug products used for the treatment of malaria, depression, anxiety and Parkinson diseases. Buchwald-Hartwig amination is the latest and well-known reaction for Pd catalyzed direct synthesis of N-aryl piperazine from aryl halides. Although several Pd-ligand systems have already been discovered for this conversion, Pd nanoparticles are recently being used for this useful coupling reaction due to their recyclability and durability. Metal nanoparticles show enhanced catalytic activity compared to their bulk counterparts due to increased surface area at the edges and corners. The use of green algal extract in place of chemical ligands makes this process more environment-friendly and cost-effective. In this research, Pd nanoparticles synthesized using green alga C. Vulgaris were utilized as an alternative approach for the coupling reaction during the preparation of N-aryl piperazines.
Methods: Synthesized Pd nanoparticles from C. Vulgaris were characterized by FTIR, SEM and XRD techniques. The catalytic activity of the synthesized nanoparticles was monitored for the synthesis of N-aryl piperazines by Buchwald-Hartwig reaction. The synthesized N-aryl piperazines were characterized by NMR, FTIR and mass analysis.
Results: A very good catalytic activity of the synthesized Pd nanoparticles from green alga Chlorella vulgaris extract was observed. The green alga not only reduces the size of the Pd metal to nanoparticles but also acts as a green ligand for reduction of Pd(II) to Pd(0) during nanoparticle synthesis. Using this Pd nanoparticles-green ligand system, several N-aryl piperazines were synthesized in good to excellent yields. Reaction conditions for better conversion were optimized. The comparative advantage of the catalytic system with recently published works on Buchwald-Hartwig C-N coupling reaction is given. Recyclability and durability of the catalyst were explored and the results were found to be promising. A plausible mechanism of Pd nanoparticle catalyzed reaction is also proposed.
Conclusion: Catalytic activity of the Pd nanoparticle synthesized from Chlorella vulagris in the synthesis of N-aryl piperazines by Buchwald-Hartwig reaction is reported first time to the best of our knowledge and understanding. The green approach of Pd catalyst to facilitate the reaction and its environmental impact is the main characteristic of the process.
Keywords: Buchwald-Hartwig reaction, C-N bond formation, catalysis, green alga, N-aryl piperazine, Pd nanoparticle.
Graphical Abstract
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