Bioactive NHC-derived palladium complexes: synthesis, catalytic activity for the Suzuki-Miyaura coupling of aryl chlorides and bromides and their antibacterial activities

Abstract

Pd(II)-bis(NHC) complexes (where NHC = N-heterocyclic carbene) bearing asymmetrically and symmetrically substituted NHC-ligand have been synthesized via deprotonation of 5,6-dimethylbenzimidazolium salts. The NHC precursors have been achieved via the two step N-alkylation of 5,6-dimethylbenzimidazole. The resultant salts were deprotonated with PdCl₂ and K₂CO₃ in dry THF for 2(a–e). The obtained complexes were identified and characterized by ¹H and ¹³C NMR, FT-IR, DART-TOF mass spectrometry and elemental analysis. These new Pd(II)-bis(NHC) complexes were applied as catalyst precursors for Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides with phenylboronic acid to afford the corresponding products in good yields. This catalytic reaction was evaluated in the presence of KOtBu/toluene. The antibacterial activities of 2(a–e) were investigated against Gram (+)/(−) bacteria using the agar dilution procedure. The antibacterial activities of 2 vary with the nature of the ligands; MIC values of 2(a–e) were determined.

Keywords:

• Suzuki-Miyaura coupling
• N-heterocyclic carbene
• Pd(II)-bis(NHC) catalyst
• antibacterial activity

Acknowledgements

This work was funded by the Research Supporting Project (RSP-2019/75), King Saud University, Riyadh, Saudi Arabia.

Disclosure statement

No potential conflict of interest was reported by the authors.