Hydrogenation and N-alkylation of anilines and imines via transfer hydrogenation

What is it about?

The nickel-catalyzed N-alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the CvN bond reduction and N-alkylation of a variety of imines with ethanol, the latter acting as a hydrogen and acetaldehyde source, which allowed for the reduction and subsequent condensation to yield the corresponding N-alkylated products.

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Why is it important?

We disclose herein our results dealing with the N-alkylation of anilines and the CvN bond reduction and N-alkylation of imines, with nickel catalysts, without basic additives and H2. These experiments used P-donor ancillary ligands and several alcohols, such as ethanol, methanol and 2-propanol, which acted as solvents and reagents in the reaction.