Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes was written by Liu, Richard Y.;Bae, Minwoo;Buchwald, Stephen L.. And the article was included in Journal of the American Chemical Society in 2018.Electric Literature of C13H24N2O This article mentions the following:
Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. A copper-hydride(CuH)-catalyzed process is reported that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups and can be performed using a simple ligand, inexpensive siloxanes and low catalyst loading. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Electric Literature of C13H24N2O).
1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Electric Literature of C13H24N2O
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics