615253-71-9

Upstream product

• 123-75-1 pyrrolidine 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 155059-95-3 1-(1-phenylprop‐2-yn-1‐yl)pyrrolidine 
• 98-86-2 acetophenone 
• 611-73-4 Benzoylformic acid 
• 4890-63-5 (phenylethynyl)magnesium chloride 
• 618-31-5 benzylidene dibromide 
• 100-51-6 benzyl alcohol 

Downstream Products

• 6307-20-6 2,3,5-triphenylfuran 
• 3780-00-5 1-(3-phenyl-1,2-propadienyl)benzene 

Relevant academic research and scientific papers

Synthesis of propargylamines by three-component coupling of aldehydes, amines and alkynes catalyzed by magnetically separable copper ferrite nanoparticles

An efficient three-component coupling of aldehydes, amines and alkynes has been developed to prepare propargylamines in nearly quantitative yields using magnetically separable copper ferrite nanoparticles as catalyst. Structurally divergent aldehydes and

Covalently immobilized indium(III) composite (In/SiO2) as highly efficient reusable catalyst for A3-coupling of aldehydes, alkynes and amines under solvent-free conditions

We describe the synthesis and application of a silica-xerogel-supported indium(III) composite (In/SiO2). Using X-ray photoelectron spectroscopy, by the first time it was possible to identify that the indium is bonded to the silica through coval

Heterocyclic thiolates and phosphine ligands in copper-catalyzed synthesis of propargylamines in water

The product obtained by reaction of deprotonation of 2-mercaptobenzothiazole or methimazole (2-mercapto-1-methylimidazole) with copper iodide in the presence of tertiary phosphines, PR2R' (R = R' = cyclohexyl; R = R' = phenyl; R = phenyl, R' = methyl) showed high catalytic activity in A3 coupling of a series of aldehydes with phenylacetylene and piperidine, yielding propargylamines. An investigation into the nature of active species carried out mainly by electrospray ionization mass spectrometry (ESI-MS) techniques underscores a crucial role played by organosulfur and organophosphorus compounds in the generation of active species responsible for these reactions. The coupling reactions were successfully carried out at low catalyst loadings in water/THF (20:1) and in relatively short reaction times. The scope of the reaction was also investigated with 20 examples.

Structural and Electronic Control of the Bidentate 1-(2-pyridyl)benzotriazole Ligand in Copper Chemistry with Application to Catalysis in the A3 Coupling Reaction

The hybrid bidentate 1-(2-pyridyl)benzotriazole (pyb) ligand was introduced into 3d transition metal catalysis. Specifically, [CuII(OTf)2(pyb)2]?2 CH3CN (1) enables the synthesis of a wide range of propargylamines by the A3 coupling reaction at room temperature in the absence of additives. Experimental and high-level theoretical calculations suggest that the bridging N atom of the ligand imposes exclusive trans coordination at Cu and allows ligand rotation, while the N atom of the pyridine group modulates charge distribution and flux, and thus orchestrates structural and electronic precatalyst control permitting alkyne binding with simultaneous activation of the C?H bond via a transient CuI species.

Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition

Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore, plausible mechanisms for the synthesis of different products have been proposed.

Biradicalo-iminobenzosemiquinonato(1?) complexes of nickel(ii): catalytic activity in three-component coupling of aldehydes, amines and alkynes

The six-coordinated bis-o-iminosemiquinone complex,NiL2BIS, in whichLBISis theo-iminosemiquinone 1-electron oxidized form of the tridentateo-aminophenol benzoxazole-based ligandH2LBAP, was synthesized

Discrete Benzotriazole-Copper(II) Complexes in Chelated and Non-Chelated Coordination Modes: Structural Analysis and Catalytic Application in Click and A3 Coupling Reactions

Two copper(II) complexes with benzotriazole-based ligands having pyridyl and quinolinyl arms were synthesized in good yields and characterized fully via spectroscopic and crystallographic techniques. The crystal structures of the complexes revealed differ

Heavy metal removing by modified bentonite and study of catalytic activity

Due to the high hydrophobicity and surface area, clays are efficient adsorbents for the removal of liquid impurities and purification of gases when they are modified. In this work, bentonite was modified with imidazole and imidazolium groups and resulting clays were characterized by different techniques such as 1H NMR, 13C NMR, TEM, SEM, XPS, TG, and FT-IR. Applications of these clays were studied in the removal of Co, Cu, and Pb in the wastewater. Effects of contact time, pH, initial heavy metal ions concentration, and kinetic were investigated. The catalytic activity of the metals adsorbed by imidazole modified bentonite was studied in A3 coupling reactions of various amines, aldehydes, and alkynes.

Silver chloride supported on Vitamin B1 -Organometallic magnetic catalyst: synthesis, density functional theory study and application in A3-coupling reactions

A highly efficient Fe3O4@VitB1–Ag(I) magnetic catalyst has been obtained using surface modification of Fe3O4. To this end, silver chloride was immobilized on Fe3O4 nanoparticles

Gold nanoparticles stabilized by PEG-tagged imidazolium salts as recyclable catalysts for the synthesis of propargylamines and the cycloisomerization of γ-alkynoic acids

We report the synthesis of PEGylated imidazolium (bromide and tetrafluoroborate) and tris-imidazolium (bromide) salts containing triazole linkers, and their use as stabilizers for the preparation of water-soluble gold nanoparticles by reduction of tetrachloroauric acid with sodium borohydride. The nanomaterials have been characterized. The X-Ray Photoelectron Spectroscopy (XPS) indicated the presence of Au(i) and Au(0) species, the oxidized form being more abundant in the nanomaterial derived from the tris-imidazolium bromide. The catalytic activity of these gold nanoparticles has been proved in the A3 coupling between carbonyl compounds, terminal alkynes and amines to afford propargylamines, and in the cycloisomerization of γ-alkynoic acids to enol lactones. The nanomaterial derived from the PEG-tagged tris-imidazolium bromide provided the best performance and it has been recycled in both reactions (up to four and six runs) taking advantage of its solubility properties.