1017-73-8Relevant academic research and scientific papers
Rh(I)-catalyzed CO gas-free cyclohydrocarbonylation of alkynes with formaldehyde to α,β-butenolides
Fuji, Koji,Morimoto, Tsumoru,Tsutsumi, Ken,Kakiuchi, Kiyomi
, p. 3295 - 3297 (2005)
The rhodium(I)-catalyzed reaction of alkynes with formaldehyde proceeds via the double incorporation of a carbonyl moiety from formaldehyde, resulting in a CO gas-free cyclohydrocarbonylation leading to α,β-butenolides. The Royal Society of Chemistry 2005.
Microwave-assisted copper(I) catalyzed A3-coupling reaction: Reactivity, substrate scope and the structural characterization of two coupling products
Kashid, Vitthalrao S.,Balakrishna, Maravanji S.
, p. 78 - 82 (2018)
The application of highly efficient catalyst [{Cu(μ ? I)2Cu}(PPh3)4] for the synthesis of biologically and pharmaceutically important propargylamine derivatives through microwave assisted A3-coupling reaction is
Nano Ag-doped magnetic-Fe3O4@mesoporous TiO2 core–shell hollow spheres: synthesis and enhanced catalytic activity in A3 and KA2 coupling reactions
Elhampour, Ali,Nemati, Friuozeh,Heravi, Majid M.
, p. 1793 - 1805 (2017)
Abstract: Nano Ag-doped Fe3O4@mesoporous TiO2 core–shell hollow spheres (h-Fe3O4@m-TiO2/Ag) were efficiently prepared. They were fully characterized by FT-IR, FE-SEM, EDX, ICP, TGA, XRD, and BET methods. In addition, their magnetic properties were determined by means of the VSM method. Also, the ρshell of the prepared hollow Fe3O4 micro-particles was calculated, being found just slightly lighter than that of solid sphere-like Fe3O4. The catalytic activity of this novel catalyst system was successfully examined as a novel catalyst system in A3 coupling reactions (aldehyde?+?amine?+?acetylene). This highly active magnetic catalyst was easily separated using an external magnet and re-used in five consecutive runs in the model reaction without appreciable loss of its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
Zn(OTf)2-Mediated Expeditious and Solvent-Free Synthesis of Propargylamines via C-H Activation of Phenylacetylene
Sarode, Prashant B.,Bahekar, Sandeep P.,Chandak, Hemant S.
, p. 2209 - 2212 (2016)
Zn(OTf)2-mediated expeditious and solvent-free synthesis of propargylamines via A3 coupling of aldehydes, amines, and phenylacetylene has been described. The described protocol proceeds effectively with variety of substituted benzaldehydes, enolizable aldehyde, and formaldehyde. Recyclability of the catalyst, low catalyst loading, and use of inexpensive catalyst are the key features of the present protocol.
Synthesis of 2,3-acetylenic amines by aminomethylation of acetylenes with geminal diamines
Shaibakova,Titova,Makhmudiyarov,Ibragimov,Dzhemilev
, p. 43 - 48 (2010)
A general and effective procedure has been developed for the synthesis of symmetrical and unsym- metrical 2,3-acetylenic amines by aminomethylation of terminal mono- and diacetylenes with geminal diamines in the presence of transition metal salts and complexes.
Copper(II) carboxymethylcellulose (CMC-CuII) as an efficient catalyst for aldehyde-alkyne-amine coupling under solvent-free conditions
Liu, Xiaoping,Lin, Bijin,Zhang, Zhuan,Lei, Hao,Li, Yiqun
, p. 94399 - 94407 (2016)
A novel and eco-friendly three-component reaction of aldehydes, amines, and alkynes (A3 coupling) catalyzed by a recoverable copper(ii) carboxymethylcellulose (CMC-CuII) catalyst has been developed, producing a diverse range of propargylamines under solvent-free conditions in good yields. The CMC-CuII catalyzed reaction is especially effective for reactions involving aromatic and aliphatic aldehydes. High catalytic activity was obtained in the presence of 5 mol% CMC-CuII without any other co-catalyst, additives, or bases under aerobic conditions. Moreover, the catalyst can be easily recovered and reused for at least four cycles without significant decrease in its catalytic activity.
Magnetically recoverable graphene-based nanocomposite material as an efficient catalyst for the synthesis of propargylamines: Via A3 coupling reaction
Hussain, Najrul,Das, Manash R.
, p. 12756 - 12766 (2017)
The magnetically separable Au NPs-Fe3O4-rGO catalyst provides a robust and efficient route for the A3 coupling reaction of secondary amines, terminal alkynes and aldehyde with tolerance of diverse functional groups for the
Stable mesoporous Fe/TiO2 nanoparticles: A recoverable catalyst for solvent-free synthesis of propargylamine via C[sbnd]H activation
Kotadia, Deepali A.,Soni, Saurabh S.
, p. 231 - 238 (2014)
Fe-doped mesoporous metal oxides (Fe/MO2, M = Si and Ti) were synthesized with particle size in the range of 10–15 nm via modified sol–gel method. The Fe modified SiO2 and TiO2 have proved to be very efficient catalysts in three-component coupling of aldehydes, alkynes and amines for the solvent-free synthesis of proargylamines. Among the two Fe-doped metal oxide catalysts, Fe/TiO2 gives 94% propargylamine yield at 245 W microwave power for few minutes under solvent free condition and found to be a better catalyst. With a Fe/TiO2 heterogeneous catalyst and in the absence of solvent, the proposed process for propargylamine synthesis is green and environmentally benign protocol.
NbCl5-Mg reagent system in regio-and stereoselective synthesis of (2Z)-alkenylamines and (3Z)-alkenylols from substituted 2-alkynylamines and 3-alkynylols
Dzhemilev, Usein M.,Gabdullin, Azat M.,Kadikova, Rita N.,Mozgovoj, Oleg S.,Ramazanov, Ilfir R.
, (2021)
The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5 –Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio-and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems—NbCl5-Mg and TaCl5-Mg, in relation to oxygen-and nitrogen-containing alkynes. A regio-and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene.
Nano copper(I) oxide-zinc oxide catalyzed coupling of aldehydes or ketones, secondary amines, and terminal alkynes in solvent-free conditions
Hosseini-Sarvari, Mona,Moeini, Fatemeh
, p. 624 - 635 (2014)
A simple, efficient, and environmentally benign method has been described for the synthesis of propargylamines through a one-pot three-component coupling reaction of terminal alkynes, aldehydes or ketones, and secondary amines in excellent isolated yields, under solvent-free conditions, using a catalytic amount of nano Cu2O-ZnO as the recyclable, and heterogeneous catalyst. The catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for ten successive runs. The catalyst was characterized by using powder X-ray diffraction (XRD), a transmission electron microscopy (TEM), a scanning electron microscopy (SEM), BET surface area measurement and FT-IR spectroscopy.
