58265-40-0

Upstream product

• 116-53-0 2-Methylbutanoic acid 
• 100-46-9 benzylamine 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 622-79-7 benzyl azide 
• 121537-89-1 C₁₀H₁₈O₄ 
• 19919-46-1 3-benzyl-4-ethyl-5-methyl-4,5-dihydro-3H-[1,2,3]triazol-4-ol 

Relevant academic research and scientific papers

Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines

A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.

Catalytic acceptorless dehydrogenations: Ru-Macho catalyzed construction of amides and imines

A commercially available ruthenium(II) PNP type pincer catalyst (Ru-Macho) promotes formation of amides and imines from alcohols and amines via an acceptorless dehydrogenation pathway. The formation of secondary amides, tertiary amides, and secondary ketimines occurs in yields ranging from 35% to 95%.

Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines

A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.

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.

Dehydrogenative amide synthesis: Azide as a nitrogen source

A new atom-economical strategy to amide linkage from an azide and alcohol liberating hydrogen and nitrogen was developed with an in situ generated ruthenium catalytic system. The reaction has broad substrate generality including diols for the synthesis of cyclic imides.

PROCESS OF FORMING AN AMIDE

A process is provided for the synthesis of an amide. A primary or secondary amine and a primary alcohol, with the amine and the alcohol being either moieties of different reactants or moieties of the same molecule, are contacted in the presence of a Ruthenium (II) catalyst. The Ruthenium (II) catalyst is free of a phosphine ligand. The process is also carried out in the absence of a phosphine. Providing the Ruthenium (II) catalyst includes providing an N-heterocyclic carbene.

N-heterocyclic carbene based ruthenium-catalyzed direct amide synthesis from alcohols and secondary amines: Involvement of esters

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).

Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)-N′-benzyl 2-amino-3-methylbutanamide

Primary amino acid derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to functionalized amino acids (FAAs) (N′-benzyl 2-substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model, and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogues of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s).

Weil-defined N-heterocyclic carbene based ruthenium catalysts for direct amide synthesis from alcohols and amines

Well-defined N-heterocyclic carbene based ruthenium, complexes were developed as highly active catalysts for direct amide synthesis from alcohols and amines. A catalytic amount of a base such, as KO1Bu was essential to initiate the catalytic cycle. Activity of the Ru complexes was comparable with the reported in situ Ru catalysts. These catalysts provided mechanistic insight suggesting a Ru hydride species as an active catalytic intermediate. The generation of the Ru hydride was critical for the amidation of free aldehydes.

Simple RuCl3-catalyzed amide synthesis from alcohols and amines

A catalyst for the direct synthesis of amides from amines and alcohols, generated in situ from the economically attractive and readily available RuCl3, an N-heterocyclic carbene (NHC), and pyridine, was developed. Of the screened NHC precursors, a less bulky one gave better yields for modestly sterically hindered substrates. In a search for the true catalytic intermediates, Grubbs catalysts were found to be active for the amidation of alcohols under basic conditions, suggesting that an Ru complex supported by an NHC ligand can catalyze the reaction.