Synthesis of β-hydroxyamides through ruthenium-catalyzed hydration/transfer hydrogenation of β-ketonitriles in water: Scope and limitations

A cascade process for the straightforward one-pot conversion of beta-ketonitriles into beta-hydroxyamides is presented. The process, that proceeds in water employing the arene-ruthenium(II) complex [RuCl2(eta(6)-p-cymene){P(4-C6H4F)(2)Cl}] as catalyst in combination with sodium formate, involves the initial hydration of the beta-ketonitrile substrates to generate the corresponding beta-ketoamide intermediates, which subsequently undergo the transfer hydrogenation (TH) of the carbonyl group. Employing a family of forty different beta-ketonitriles, featuring diverse substitution patterns, the scope and limitations of the process have been established. (c) 2019 Elsevier B.V. All rights reserved.