Mechanism study on Raney nickel-catalyzed amination of resorcinol

•Raney Ni catalyze amination of resorcinol with secondary amines: a density functional theory study

Amination of resorcinol catalyzed by Raney nickel has been examined with good yield. Using the first principle density functional theory, some detailed mechanism of the amination of resorcinol on the Ni(111) surface is explored. The resorcinol is adsorbed on the Ni surface at the hollow site to form ketone by isomerization. The isomerization has a barrier of 122.1 kJ/mol. Ketone can couple with secondary amine mediated by resorcinol to afford hemiaminal. For the formation of hemiaminal, the steric effect of the alkyl group of secondary amine is obvious. Hemiaminal undergoes dehydration to get final product, which occurs by the preferred adsorption in the bridge site, cleavage of CO bond initially, followed by subsequent cleavage of CH bond.

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