Hg(II) and Ru(II) complexes of mono- and dichalcogenides of bis(diphenylphosphino)amine chelating ligands: Synthesis, characterization and catalytic activity in transfer hydrogenation of acetophenone derivatives

Abstract

Reactions of C₁₀H₇-1-N(PPh₂)₂ (1) and C₁₀H₇-1-N(P(Se)Ph₂)₂ (2) ligands with mercury(II)iodide in equimolar ratio gave cis-[HgI₂{1-κ²P,P}] (3) and cis-[HgI₂{2-κ²Se,Se}] (4). Also, refluxing of monooxidized thioyl and selenoyl bis(phosphino)amine ligands C₁₀H₇-1-N(P(E)Ph₂)(PPh₂) (E = S (5), Se (6)) with [Ru(CO)₃Cl₂]₂ dimer afforded cis-[Ru(CO)₂Cl₂{5-κ²P,S}] (7) and cis-[Ru(CO)₂Cl₂{6-κ²P,Se}] (8). Complexes 3, 4, 7 and 8 were identified and characterized by multinuclear NMR (¹H, ¹³C, ³¹P and ⁷⁷Se NMR) and IR spectroscopy. The molecular structure of 5 was determined by single X-ray crystallography. 5 is the first structurally characterized example of this kind of κ²P,S -bidentate ligand. The novel ruthenium(II) complexes 7 and 8 show high catalytic activity in the transfer hydrogenation of acetophenone derivatives to 1-phenylethanol derivatives in the presence of 2-propanol as the hydrogen source.

Graphical Abstract

Keywords:

• Bis(diphenylphosphino) amine
• mercury
• ruthenium
• catalysis
• transfer hydrogenation

Acknowledgments

We would like to thank Dr. Munther Khanfer for collecting the X-ray data and Dr. Ziad Moussa for performing GC analysis. The X-ray of compound 5 was provided by Homdi Mango Research center (HMRC), Jordan University, Jordan. Also, we gratefully acknowledge J.U.S.T., U. A. E. U. and Hashimiate Universities for various supports.