Ruthenium complexes with triazenide ligands bearing an N-heterocyclic moiety, and their catalytic properties in the reduction of nitroarenes

• Published in: RSC advances Vol. 14; no. 33; pp. 24019 - 24030
• Main Authors: Romero-Soto, Christian A, Iglesias, Ana L, Velázquez-Ham, Amor F, Camarena-Díaz, Juan P, Correa-Ayala, Erick, Gomez-Lopez, Jessica L, Chávez, Daniel, Ochoa-Terán, Adrián, Aguirre, Gerardo, Rheingold, Arnold L, Grotjahn, Douglas B, Parra-Hake, Miguel, Miranda-Soto, Valentín
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 26-07-2024; The Royal Society of Chemistry
• Subjects: Amines; Aniline; Aromatic compounds; Catalysis; Chemical synthesis; Chemistry; Ethanol; Ligands; Magnetic properties; Mass spectrometry; Nitrobenzene; NMR; Nuclear magnetic resonance; Organic compounds; Room temperature; Ruthenium compounds
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d4ra04813j

A series of ruthenium complexes of formulae [RuCl(triazenide)(
-cymene)] have been synthesized using as ligand a triazenide monofunctionalized with an N-heterocyclic moiety. Nuclear magnetic resonance, high resolution mass spectrometry and X-ray diffraction were used to characterize the triazenide ligands and their complexes. In addition, these ruthenium complexes catalyzed the reduction of nitrobenzene to aniline in the presence of sodium borohydride and ethanol as solvent at room temperature. Notably, complex 5 was especially active in the reduction of nitroarenes substituted at the aromatic ring with electron-withdrawing or electron-donating fuctional groups affording the desired arylamines in good to excellent yields (80-100%). The role of the N-heterocyclic moiety on catalysis was explored.