87143-88-2

Upstream product

• 536-74-3 phenylacetylene 
• 611-74-5 N,N-dimethylbenzamide 
• 758-16-7 N,N-dimethylthioformamide 
• 4440-01-1 lithium phenylacetylide 
• 103-83-3 N,N'-dimethylbenzylamine 
• 13120-03-1 N,N-dimethylselenobenzamide 
• 100-58-3 phenylmagnesium bromide 
• 107-97-1 sarcosine 
• 100-52-7 benzaldehyde 
• 124-40-3 dimethyl amine 
• 622-29-7 N-Benzylidenemethylamine 
• 20599-29-5 (α-butoxy-benzyl)-dimethyl-amine 
• 13146-23-1 copper(I) phenylacetylenide 
• 59836-47-4 N,N-dimethyl-benzylideneammonium iodide 

Downstream Products

• 67134-56-9 2-benzyl-1-methyl-3-phenyl-1H-indole 
• 114461-01-7 (1,3-Diphenyl-prop-2-ynyl)-trimethyl-ammonium; iodide 

Relevant academic research and scientific papers

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.

Aromatic Aza-Claisen Rearrangement of Arylpropargylammonium Salts Generated in situ from Arynes and Tertiary Propargylamines

The charge-accelerated aza-Claisen rearrangement of ammonium salts serves as a key step in the construction of complex nitrogen-containing molecules. However, much less attention has been paid to the aromatic aza-Claisen rearrangement than to the aliphatic one. Herein, we report an unprecedented aromatic aza-Claisen rearrangement of arylpropargylammonium salts, generated in situ from arynes and tertiary propargylamines, delivering structurally diverse 2-propargylanilines in moderate to good yields with high regioselectivity. This rearrangement proceeds in the absence of strong bases or transition metals, is compatible with moisture and air, tolerates a wide variety of functional groups, and is amenable to forming 11- to 13-membered heterocycles with a triple bond. The 2-propargylaniline products were treated with aluminum chloride in ethanol to afford multisubstituted indoles in moderate to excellent yields. Finally, a series of deuterium-labeling experiments was performed to elucidate the reaction mechanism.

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.

Caffeine gold complex supported on magnetic nanoparticles as a green and high turnover frequency catalyst for room temperature A3 coupling reaction in water

A new heterogeneous catalyst derived from gold (III) and supported on caffeine-coated magnetic nanoparticles, Fe3O4@Caff-Au, has been prepared and characterized using different techniques. This magnetic gold composite shows high catalytic activity in A3 coupling reactions of terminal alkynes, aldehydes and secondary amines. Using this green catalyst, propargylamines are obtained in high turnover frequency in short reaction times using water as solvent at room temperature. This stable and ready accessible catalyst can be easily recycled magnetically for at least nine consecutive runs without significant loss of activity and with slight aggregation of Au species.

Gold Nanoparticles Supported on Imidazole-Modified Bentonite: Environmentally Benign Heterogeneous Catalyst for the Three-Component Synthesis of Propargylamines in Water

Gold nanoparticles supported on imidazole-modified bentonite, Bent@Im@Au NPs, has been developed for the first time as an effective heterogeneous catalyst for the synthesis of propargylamines under mild reaction conditions in water at a loading of 0.07 mol % of Au. Various techniques such as X-ray diffraction, high-resolution transmission electron microscopy, Fourier transform infrared spectroscopy, and element mapping by scanning electron microscopy were used to determine the physicochemical properties of the catalysts. The new gold catalyst was found to be highly active providing high to excellent yields of A3 coupling products via the reactions of various aldehydes, having electron-withdrawing as well as electron-donating substituents, with different amines and alkynes. The catalysts can be easily recovered and reused without significant loss of activity and the recycled catalyst was characterized.

Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(i) bis-metal sequential catalysis

We report herein a convenient and versatile method for the direct reductive alkynylation of tertiary amides to give propargylic amines through sequential Ir-catalysed hydrosilylation-Cu(i)-catalysed alkynylation. The reactions proceed chemoselectively at the amide group in the presence of several sensitive functional groups including the very reactive aldehyde group on either the amide or the alkyne coupling partner. The method is general for tert-amides with or without α-hydrogen.

Nontraditional reactions of azomethine ylides: Decarboxylative three-component couplings of α-amino acids

(Formula Presented) New reactions of azomethine ylides with nontraditional dipolarophiles are reported. Azomethine ylides, formed in situ via decarboxylative condensations of α-amino acids with aldehydes, undergo reactions with naphthols, indoles, alkynes

Aldehyde- and ketone-induced tandem decarboxylation-coupling (Csp 3-Csp) of natural α-amino acids and alkynes

(Chemical Equation Presented) An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp3-Csp) catalyzed by copper with use of natural α-amino acids as starting materials is developed under neutral condition

Copper(0)-induced deselenative insertion of N,N-disubstituted selenoamides into acetylenic C-H bond leading to propargylamines

Upon heating at 110 °C in the presence of copper(0) powder, terminal acetylenes undergo a novel deselenative C-H bond insertion reaction of N,N-disubstituted selenoamides, affording the corresponding propargylamines in good to excellent yields, selectivel

Copper/diethyl azodicarboxylate Mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne

Mediated by copper/diethyl azodicarboxylate, regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne was successfully established. It is not necessary for the tertiary methylamines to be aryl substituted to modulate