N-Heterocyclic carbene-Pd(II)-PPh₃ complexes as a new highly efficient catalyst system for the Sonogashira cross-coupling reaction: Synthesis, characterization and biological activities

Abstract

A novel series of N-heterocyclic carbene-phosphine palladium(II) complexes has been synthesized and fully characterized by IR, ¹H NMR, ¹³C NMR, and ³¹P NMR spectroscopies, and elemental analysis. The new N-heterocyclic carbene (NHC)-phosphine palladium(II) complexes 3a–h have been easily prepared by the reaction of the corresponding PEPPSI (pyridine-enhanced precatalyst preparation stabilization and initiation) complexes 2a–h and triphenylphosphine in dichloromethane in high yields. These complexes were applied as catalyst precursors which efficiently catalyzed Sonogashira reactions between aryl bromides and phenylacetylene to afford the corresponding products in good yields. The bulky NHC-Pd-PPh₃ complexes 3 were tested against Gram-positive and Gram-negative bacteria to study their biological activity. All the complexes exhibit antibacterial against these organisms. Investigation of the anti-acetylcholinesterase activity of the studied complexes showed that compounds 3a and 3b exhibited moderate activity at 100 μg mL⁻¹ and product 3b is the most active.

Keywords:

• N-Heterocyclic carbine
• Sonogashira reaction
• palladium catalyst
• biological activities