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C‐N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N‐Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines

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Ruthenium nanoparticles (NPs) supported on N‐doped carbon (Ru/N−C) were prepared by the pyrolysis of cis‐Ru(phen)2Cl2 loaded onto carbon powder (VULCAN XC72R) at 800 °C. Ru/N−C NPs (0.2 mol% Ru) selectively catalyzed either… Click to show full abstract

Ruthenium nanoparticles (NPs) supported on N‐doped carbon (Ru/N−C) were prepared by the pyrolysis of cis‐Ru(phen)2Cl2 loaded onto carbon powder (VULCAN XC72R) at 800 °C. Ru/N−C NPs (0.2 mol% Ru) selectively catalyzed either acceptorless dehydrogenation coupling (ADC) or auto‐transfer‐hydrogen (ATH) reactions of amines with alcohols to imines and secondary amines. Such selectivity could be controlled by the choice of alkali metal ion associated with the base. Under similar catalytic conditions, the ADC cross‐coupling of diamines with primary alcohols or diols afforded the corresponding benzimidazoles and quinoxalines in good to excellent yields. This catalytic system displayed good activity, recyclability, and wide applicability to a diverse range of substrates.

Keywords: doped carbon; carbon; ruthenium nanoparticles; secondary amines; supported doped; acceptorless dehydrogenation

Journal Title: ChemCatChem
Year Published: 2018

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