10264-30-9Relevant academic research and scientific papers
Direct amide synthesis from alcohols and amines by phosphine-free ruthenium catalyst systems
Ghosh, Subhash Chandra,Muthaiah, Senthilkumar,Zhang, Yao,Xu, Xiangya,Hong, Soon Hyeok
, p. 2643 - 2649 (2009)
Amides are synthesized directly from alcohols and amines in high yields using an in situ generated catalyst from easily available ruthenium complexes such as the (p-cymene)ruthenium dichloride dimer, [Ru(p-cymeme)Cl 2]2, or the (benz
The selective reaction of primary amines with carbonyl imidazole containing compounds: Selective amide and carbamate synthesis
Rannard, Steve P.,Davis, Nicola J.
, p. 2117 - 2120 (2000)
matrix presented A new highly selective synthesis of amides and carbamates is described. In both cases the syntheses involve the formation of carbonyl imidazole intermediates which subsequently undergo previously unreported selective reactions with primary amines. Acid imidazolides with sufficient chain length will exclusively react with primary amines even in the presence of secondary and tertiary functionality. The imidazole carboxylic esters of secondary or tertiary alcohols also react selectively with primary amines, forming controlled carbamate structures.
Direct amide synthesis from either alcohols or aldehydes with amines: Activity of Ru(II) hydride and Ru(0) complexes
Muthaiah, Senthilkumar,Ghosh, Subhash Chandra,Jee, Joo-Eun,Chen, Cheng,Zhang, Jian,Hong, Soon Hyeok
, p. 3002 - 3006 (2010)
An in situ generated catalyst from readily available RuH 2(PPh3)4, an N-heterocyclic carbene (NHC) precursor, NaH, and acetonitrile was developed. The catalyst showed high activity for the amide synthesis directly from either alcohols or aldehydes with amines. When a mixture of an alcohol and an aldehyde was reacted with an amine, both of the corresponding amides were obtained with good yields. Homogeneous Ru(0) complexes such as (4-1,5-cyclooctadiene)(6-1,3,5- cyclooctatriene)ruthenium [Ru(cod)(cot)] and Ru3(CO)12 were also active in the amidation of an alcohol or an aldehyde with the help of an in situ generated NHC ligand.
Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment
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Paragraph 0047-0050, (2021/01/24)
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.
N-Heterocyclic carbene-based well-defined ruthenium hydride complexes for direct amide synthesis from alcohols and amines under base-free conditions
Kim, Kunsoon,Kang, Byungjoon,Hong, Soon Hyeok
, p. 4565 - 4569 (2015/06/08)
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-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy
Kang, Byungjoon,Fu, Zhenqian,Hong, Soon Hyeok
supporting information, p. 11704 - 11707 (2013/09/02)
A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrile is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the α-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single byproduct. A utility of the reaction was demonstrated by synthesizing 13C or 15N isotope-labeled amides without involvement of any separate reduction and oxidation step.
Dehydrogenative amide synthesis: Azide as a nitrogen source
Fu, Zhenqian,Lee, Jeongbin,Kang, Byungjoon,Hong, Soon Hyeok
supporting information, p. 6028 - 6031 (2013/02/22)
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
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Page/Page column 20-24, (2011/04/19)
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.
METHOD FOR PREPARATION OF AMIDES FROM ALCOHOLS AND AMINES BY EXTRUSION OF HYDROGEN
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Page/Page column 9, (2012/01/13)
The present invention relates to a method for preparation of carboxamides using alcohols and amines as starting materials in a dehydrogenative coupling reaction catalyzed by a ruthenium N-heterocyciic carbene (NHC) complex, which may be prepared in situ.
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).
