615253-68-4

Upstream product

• 123-75-1 pyrrolidine 
• 536-74-3 phenylacetylene 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 67647-93-2 (R)-(3-cyclohexylpropa-1,2-dien-1-yl)benzene 
• 67647-93-2 (S)-3-cyclohexyl-1-phenyl-1,2-propadiene 
• 67647-93-2 (3-cyclohexylpropa-1,2-dien-1-yl)benzene 

Relevant academic research and scientific papers

The First Silver-Catalyzed Three-Component Coupling of Aldehyde, Alkyne, and Amine

(Equation presented) Silver iodide catalyzed the three-component coupling of aldehyde, alkyne, and amines to generate propargylic amines with high efficiency in water. The silver-catalyzed reaction is especially effective for reactions involving aliphatic

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.

Breaking the symmetry:C1-salans with (N-H) backbones

We disclose a synthetic route that providess an unprecedented library ofC1salan ligands endowed with (N-H) backbones, previously limited toN-methylated backbones. Efforts to identify a generic complexation protocol to yield the corresponding Cu(ii)-salan complexes demonstrate the scope and limitations of this approach.

Shedding light on the use of Cu(ii)-salen complexes in the A3 coupling reaction

One Cu(ii) complex, {Cu(ii)L} (1S), has been synthesised, in two high yielding steps under ambient conditions, and characterised by single-crystal X-Ray diffraction (SXRD), IR, UV-Vis, circular dichroism (CD), elemental analysis, thermogravimetric analysis (TGA) and electron spray ionization mass spectroscopy (ESI-MS). This air-stable compound enables the generation, at room temperature and in open-air, of twenty propargylamines, nine new, from secondary amines, aliphatic aldehydes and alkynes with a broad scope with yields up to 99%. Catalyst loadings can be as low as 1 mol%, while the recovered material retains its structural integrity and can be used up to 5 times without loss of its activity. Control experiments, SXRD, cyclic voltammetry and theoretical studies shed light on the mechanism revealing that the key to success is the use of phenoxido salen based ligands. These ligands orchestrate topological control permitting alkyne binding with concomitant activation of the C-H bond and simultaneously acting as a template temporarily accommodating the abstracted acetylenic proton, and continuously generating, via in situ formed radicals and a Single Electron Transfer (SET) mechanism, a transient Cu(i) active site to facilitate this transformation. The scope and limitations of this protocol are discussed and presented.

A multifunctional use of bis(methylene)bis(5-bromo-2-hydroxyl salicyloylhydrazone): From metal sensing to ambient catalysis of A3 coupling reactions

The potential use of bis(methylene)bis(5-bromo-2-hydroxylsalicyloylhydrazone) as a multifunctional fluorescence sensor for Cu2+, Ni2+, Co2+ and Fe2+ ions was investigated. The optical behaviour shows an increase in an absorption band at 408 nm which can b

Ionic liquid assisted silver-catalyzed one-pot A3-coupling reactions for the synthesis of propargylamines

A series of ionic liquids with different cations and anions were synthesized and their performances for the silver catalyzed one-pot A3-coupling reactions were investigated. The selection showed that the combination of AgNO3 and ioni

Structural Diversity and Catalytic Properties in a Family of Ag(I)-Benzotriazole Based Coordination Compounds

In this work we study the coordination chemistry of a series of semirigid benzotriazole based ligands (L1-L3) along with the low coordination number but versatile AgI ions. This has led to nine new coordination compounds formulated [Ag(L1)(CF3CO2)] (1), [Ag2(L1T)2(CF3SO3)2]·2Me2CO (2), [Ag(L2T)(ClO4)(Me2CO)] (3), [Ag(L2T)(BF4)(Et2O)] (4), [Ag2(L3T)2(ClO4)2]2 (5), [Ag(L3)(NO3)] (6), [Ag2(L3T)2(CF3CO2)2] (7), [Ag2(L3T)(CF3SO3)2] (8), and [Ag2(L3T)2(CF3CF2CO2)2]·2Me2CO (9). These compounds show structural diversity including dimers (5, 7, 9) and one-dimensional (1D) (3, 4, 6) and two-dimensional (2D) (1, 2, 8) coordination polymers. The presence of the two -CH2- units between the three rigid backbones, benzotriazole/-C6H4-/benzotriazole, provides a limited, but significant, flexibility in L1-L3, influencing their variety coordination abilities. Interestingly, certain structures exhibit an isomerism effect (L1T-L3T) in the benzotriazole unit when in solid state; a series of studies are indicative of the 1,1-form which is generally dominant in solution even in cases where the crystal structure does not contain this tautomer. The homogeneous catalytic efficacy of all compounds against the well-known multicomponent A3 coupling reaction and the hydration of alkynes were investigated. Compound 4 was identified as the optimal catalyst for both reactions, promoting the multicomponent coupling as well as the alkyne hydration reaction under low loadings (0.5 and 3 mol %, respectively) and in high yields (up to 99 and 93% in each case).

Angled Vortex Fluidic Mediated Multicomponent Photocatalytic and Transition Metal-Catalyzed Reactions

The dynamic thin film formed in an angled rapidly rotating tube in a vortex fluidic device (VFD) is effective in facilitating multicomponent reactions (MCRs) as photocatalytic or metal-mediated processes. Here, we demonstrate the utility of the VFD by using two known MCRs, an Ugi-type three component reaction and an A3-coupling reaction. The Ugi-type reaction can be done in either confined or continuous-flow modes of operation of the microfluidic platform whereas the A3-coupling reaction was optimized for the confined mode of operation. The examples tested gave excellent yields with short reaction times.

Preparation of Ag-doped g-C3N4 Nano Sheet Decorated Magnetic γ-Fe2O3@SiO2 Core–Shell Hollow Spheres through a Novel Hydrothermal Procedure: Investigation of the Catalytic activity for A3, KA2 Coupling Reactions and [3?+?2] Cycloaddition

Taking advantageous of both g-C3N4 and magnetic core-shell hollow spheres, for the first time a heterogeneous and magnetically separable hybrid system was prepared through a novel and simple hydrothermal procedure and used for immobilization of bio-synthesized Ag(0) nanoparticles. The hybrid system was fully characterized by using SEM/EDS, FTIR, VSM, TEM, XRD, TGA, DTGA, ICP-AES, BET and elemental mapping analysis. The catalytic utility of the obtained system, h-Fe2O3@SiO2/g-C3N4/Ag, for promoting ultrasonic-assisted A3, KA2 coupling reactions and [3?+?2] cycloaddition has been confirmed. The results established that the catalyst could efficiently catalyze the reaction to afford the corresponding products in high yields in short reaction times. The reusability study confirmed that the catalyst could be recovered and reused for at least five reaction runs with only slight loss of the catalytic activity. The hot filtration test also proved low silver leaching, indicating the heterogeneous nature of the catalysis.

The functional ion liquid multi-component reaction to promote the synthesis of propargyl amine compounds (by machine translation)

The invention discloses a functional ionic liquid to promote multi-component reaction synthesizing propargyl amine compounds, which belongs to the propargyl amines technical field of the synthesis of the compounds. Technical proposal of the invention poin