5215-28-1Relevant academic research and scientific papers
Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex
Pandey, Pragati,Bera, Jitendra K.
supporting information, p. 9204 - 9207 (2021/09/20)
A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.
Synthesis of α-ketoamides using potassium superoxide (KO2) as an oxidizing agent
Vasudevan,Routholla, Ganesh,Teja Illa, Giri,Reddy, D. Srinivasa
, (2020/05/25)
A simple and convenient method for the synthesis of α-ketoamides by the oxidation of aryl acetamides using potassium superoxide (KO2) as an oxidizing agent is disclosed here. The scope of the developed method is successfully tested with fifteen substrates. In addition, the utility of method has been demonstrated by synthesizing an orexin receptor antagonist, a medicinally interesting compound.
Hydrative syntheses of amides from alkynes catalyzed by an Au(I) complex containing pyridyl-functionalized NHC ligand
Singh, Kuldeep,Pal, Nilay Kumar,Guha, Chirajyoti,Bera, Jitendra K.
, p. 1 - 8 (2019/02/25)
An Au(I)-NHC complex [L1AuBr] (1) with appended pyridyl group on the ligand scaffold is synthesized and its catalytic efficacy for the direct synthesis of the amide from alkyne and sodium azide in acidic water is evaluated. Catalyst 1 readily converts a wide range of internal and terminal alkynes to the corresponding amides with low catalyst loading in TFA/DCE (2 mL, 1:1 v/v) at room temperature in short reaction time (2 h) and without the use of Ag(I) additive. A related catalyst that is devoid of the pyridyl fragment displays significantly lower activity illustrating the role of the promoter ligand for water activation. Mechanistic studies reveal an initial alkyne hydration to ketone followed by the Schmidt reaction to afford the amide.
Repurposing n-butyl stannoic acid as highly efficient catalyst for direct amidation of carboxylic acids with amines
Potadar, Santoshkumar M.,Mali, Anil S.,Waghmode, Krishnakant T.,Chaturbhuj, Ganesh U.
supporting information, p. 4582 - 4586 (2018/11/27)
This is the first-time report on the repurposing n-butyl stannoic acid as a catalyst for direct amidation of carboxylic acids with amines. Notably, efficient amidation observed in comparison with all other catalytic methods reported up until now. The protocol has successfully applied to the synthesis of a variety of amides. Moderate reaction parameters, clean amidation with excellent yields of desired amides, ability to tolerate a variety of functional groups, easy product isolation; commercial availability and recyclability of the catalyst are key advantages of the current protocol.
Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation
Yu, Weijie,Yang, Shuwu,Xiong, Fei,Fan, Tianxiang,Feng, Yan,Huang, Yuanyuan,Fu, Junkai,Wang, Tao
supporting information, p. 3099 - 3103 (2018/05/22)
An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.
Nitrogen enriched mesoporous organic polymer anchored copper(ii) material: An efficient and reusable catalyst for the synthesis of esters and amides from aromatic systems
Molla, Rostam Ali,Iqubal, Md. Asif,Ghosh, Kajari,Kamaluddin,Islam, Sk. Manirul
, p. 6546 - 6559 (2015/04/14)
A new copper-grafted mesoporous poly-melamine-formaldehyde (Cu-mPMF) has been synthesized from melamine and paraformaldehyde in DMSO medium, followed by grafting of Cu(ii) at its surface. Cu-mPMF has been characterized by elemental analysis, powder XRD, HR TEM, FE-SEM, N2 adsorption study, FT-IR, UV-vis DRS, TGA-DTA, EPR spectroscopy, Raman spectroscopy and X-ray photoelectron spectroscopy (XPS). The Cu-grafted mesoporous material showed very good catalytic activity in methyl esterification of benzylic alcohols and amidation of nitriles. Moreover, the catalyst is easily recoverable and can be reused seven times without appreciable loss of catalytic activity in the above reactions. The highly dispersed and strongly bound Cu(ii) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-mPMF catalyst. Due to strong binding with the functional groups of the polymer, no evidence of leached copper from the catalyst during the course of reaction emerged, suggesting true heterogeneity in the catalytic process. This journal is
Amide bond formation via C(sp3)-H bond functionalization and CO insertion
Liu, Huizhen,Laurenczy, Gabor,Yan, Ning,Dyson, Paul J.
supporting information, p. 341 - 343 (2014/01/06)
An efficient method for the synthesis of amides via Pd-catalyzed oxidative carbonylation of C(sp3)-H bonds with CO and amines is described. The route efficiently provides substituted phenyl amides from alkanes.
An efficient protocol for the preparation of amides by copper-catalyzed reactions between nitriles and amines in water
Li, Xiaoya,Li, Zhengkai,Deng, Hang,Zhou, Xiangge
supporting information, p. 2212 - 2216 (2013/05/09)
The reactions between nitriles and amines catalyzed by Cu(OAc)2 and 2-piperidinecarboxylic acid were carried out in pure water without any other additives. A variety of substituted amides can be obtained in moderate to good yields up to 90%.
Efficient copper(II)-catalyzed transamidation of non-activated primary carboxamides and ureas with amines
Zhang, Min,Imm, Sebastian,Baehn, Sebastian,Neubert, Lorenz,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 3905 - 3909 (2012/06/04)
Amid(e) them all: Primary carboxamides and ureas react with aromatic and aliphatic amines in the presence of a copper catalyst to give a wide range of functionalized amides (see scheme). Copyright
