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Relevant academic research and scientific papers

Highly efficient preparation of amides from aminium carboxylates using N-(p-toluenesulfonyl) imidazole

Treatment of aminium carboxylates with N-(p-toluenesulfonyl)imidazole in the presence of triethylamine in DMF at 100 °C afforded the corresponding amides in good to excellent yields. N-(p-Toluenesulfonyl)imidazole proved to be a highly efficient coupling reagent for the preparation of numerous structurally diverse primary, secondary and tertiary amides.

Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment

The invention relates to a method for preparing amide compounds through ionic liquid catalysis in a high-pressure environment. According to the method, ionic liquid 1-ethyl-3-methylimidazolium acetateis used as a catalyst and a solvent, oxygen is used as an oxidizing agent, and aromatic methanol or alkyl alcohol is converted into an amide compound under the conditions of high pressure and heating. The synthesis method provided by the invention has the advantages that the raw material and technical cost is low; compared with other traditional methods, the method is safe, low in toxicity, economical and environmentally friendly; and the method has few steps, is simple and convenient to operate, is beneficial to large-scale synthesis, and has important significance for synthesis of amide compounds and large-scale industrialization of preparation.

Zirconium catalyzed amide formation without water scavenging

A scalable homogeneous metal-catalyzed protocol for direct amidation of carboxylic acids is presented. The use of 2–10?mol% of the commercially available Zr(Cp)2(OTf)2·THF results in high yields of amides at moderate temperature, using an operationally convenient reaction protocol that circumvents the use of water scavenging techniques.

Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.

N-Heterocyclic carbene-based well-defined ruthenium hydride complexes for direct amide synthesis from alcohols and amines under base-free conditions

Readily synthesized, well-defined N-heterocyclic carbene-based ruthenium(II) hydride complexes were developed for amide synthesis from alcohols and amines under base-free conditions. Diverse amides were synthesized in fair-to-excellent yields. In the case of secondary amines, where direct dehydrogenative amidation is not feasible, a catalytic amount of a base was required to promote the transamidation of esters, which are byproducts of alcohol dimerization.

Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.

Solid-supported ortho-iodoarylboronic acid catalyst for direct amidation of carboxylic acids

Amides are a ubiquitous class of organic compounds endowed with great utility. There is a need for simple and effective catalytic methods for their direct formation from carboxylic acids and amines as a way to avoid the use of coupling reagents. We have designed a recyclable resin-supported derivative of 5-methoxy-2-iodophenylboronic acid as a heterogeneous catalyst active in ambient conditions for promoting direct amidations of aliphatic carboxylic acids and amines. The optimal, practical procedure involves a simple double-filtration to isolate the amide product while separating the catalyst from residual molecular sieves.