220501-09-7Relevant articles and documents
Amide bond synthesis via silver(I) N-heterocyclic carbene-catalyzed and tert-butyl hydroperoxide-mediated oxidative coupling of alcohols with amines under base free conditions
Balaboina, Ramesh,Thirukovela, Narasimha Swamy,Vadde, Ravinder,Vasam, Chandra Sekhar
, p. 847 - 851 (2019)
We present a base free method for amide bond construction via oxidative coupling of alcohols with amines catalyzed by Silver(I) N-heterocyclic carbenes (Ag(I)-NHCs) and mediated by tert-butyl hydroperoxide (TBHP) in ethanol. The results of controlled experiments suggest that the oxidative coupling proceeds through the formation of aldehyde, then subsequent attack by amine to give hemiaminal, which can then be oxidized to amide.
N-heterocyclic carbene based ruthenium-catalyzed direct amide synthesis from alcohols and secondary amines: Involvement of esters
Chen, Cheng,Zhang, Yao,Hong, Soon Hyeok
experimental part, p. 10005 - 10010 (2012/02/05)
A well-defined N-heterocyclic carbene based ruthenium complex was developed as a highly active precatalyst for the direct amide synthesis from alcohols and secondary amines. Notably, reaction of 1-hexanol and dibenzylamine afforded 60% of the corresponding amide using our catalytic system, while no amide formation was observed for this reaction with the previously reported catalytic systems. Unlike the previously reported amidation with less sterically hindered alcohols and amines, involvement of ester intermediates was observed (Figure presented).