Copper-Catalyzed Oxidative Amidation of Aldehydes with Amine Salts: Synthesis of Primary, Secondary, and Tertiary Amides

Abstract

A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.

Shape memory polyurethanes with oxidation-induced degradation: In vivo and in vitro correlations for endovascular material applications

“…This suggests that a 1% or 1.5% H 2 O 2 solution would be a more appropriate solution for modeling degradation for these highly porous SMP scaffolds when they are used in endovascular applications, with the comparison between the H 2 O 2 concentration-dependent rates displayed in Fig. 2; the lower-than-anticipated degradation rate is most likely due to the combination of surface chemistry, high surface area, and the porosity [5,31,32]. As compared to the silk and polypropylene present at the aneurysm sites, these SMPs display reduced inflammatory response and higher neovascularization, resulting in lower numbers of macrophages and neutrophils at the implant site, which in turn results in lower levels of peroxides and superoxides, and will ultimately decrease the oxidation rate at the material surface [31–33].…”

Recent developments in oxidative esterification and amidation of aldehydes

“…The development of environmentally benign alternative methods for this transformation is required. 27 Another important approach for aldehyde amidation was reported by Leow. 28 The oxidative amidation of aromatic aldehydes was carried out using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, air as the sole oxidant, solar light simulator or 24 W household lamp as sources of energy (Scheme 23).…”

Catalytic bio–chemo and bio–bio tandem oxidation reactions for amide and carboxylic acid synthesis

“…(1) Alcohols to aldehydes to amides (cascade 1) 10 or a large excess of the aldehyde would be an attractive tool for future chemistry.…”