Computational Study of Mechanism and Thermodynamics of Ni/IPr-Catalyzed Amidation of Esters.

ABSTRACT: Nickel catalysis has shown remarkable potential in amide C⁻N bond activation and functionalization. Particularly for the transformation between ester and amide, nickel catalysis has realized both the forward (ester to amide) and reverse (amide to ester) reactions, allowing a powerful approach for the ester and amide synthesis. Based on density functional theory (DFT) calculations, we explored the mechanism and thermodynamics of Ni/IPr-catalyzed amidation with both aromatic and aliphatic esters. The reaction follows the general cross-coupling mechanism, involving sequential oxidative addition, proton transfer, and reductive elimination. The calculations indicated the reversible nature of amidation, which highlights the importance of reaction thermodynamics in related reaction designs. To sh

SUBMITTER: Ji CL 

PROVIDER: S-EPMC6222384 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature