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Kinetic Modeling of the Nickel-Catalyzed Esterification of Amides

[Image: see text] Nickel-catalyzed coupling reactions provide exciting tools in chemical synthesis. However, most methodologies in this area require high catalyst loadings, which commonly range from 10–20 mol % nickel. Through an academic-industrial collaboration, we demonstrate that kinetic modelin...

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Detalles Bibliográficos
Autores principales: Weires, Nicholas A., Caspi, Daniel D., Garg, Neil K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5504487/
https://www.ncbi.nlm.nih.gov/pubmed/28713644
http://dx.doi.org/10.1021/acscatal.7b01444
Descripción
Sumario:[Image: see text] Nickel-catalyzed coupling reactions provide exciting tools in chemical synthesis. However, most methodologies in this area require high catalyst loadings, which commonly range from 10–20 mol % nickel. Through an academic-industrial collaboration, we demonstrate that kinetic modeling can be used strategically to overcome this problem, specifically within the context of the Ni-catalyzed conversion of amides to esters. The successful application of this methodology to a multigram-scale coupling, using only 0.4 mol % Ni, highlights the impact of this endeavor.