Synthesis of α-cyano hydroxylamine via three-component reactions and Computational mechanistic study
Reaction Kinetics, Mechanisms and Catalysis (2020) 129:349–369Mohammad A Ranjbari, Hossein Tavakol
In the present report, various α-cyano hydroxylamines were synthesized via a 3-component reaction between aromatic aldehydes, phenylhydroxylamine and trimethylsilyl cyanide at room temperature. In this line, several solvents and catalysts were employed to obtain the best conditions for the reaction. Among the employed solvents and catalysts, methanol (as solvent) and NiCl2 (as catalyst) showed the highest performances. Moreover, the mechanistic details for the both steps of this reaction in the gas phase and explicit solvent (methanol) model have been studied using DFT calculations and the energy profiles for all steps were obtained. The results of these computations are in agreement with the experimental results, which showed the methanol is the best solvent and NiCl2 is the most appropriate catalyst for this reaction.