3757-16-2

Usage

InChI:InChI=1/C14H10ClNO2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(10-6-12)16(17)18/h1-10H/b2-1+

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 1878-66-6 4-chlorophenylacetic Acid 
• 555-16-8 4-nitrobenzaldehdye 
• 60430-77-5 (p-chlorobenzyl)triphenylarsonium bromide 
• 2767-70-6 (p-nitrobenzyl)triphenylphosphonium bromide 
• 1073-67-2 4-vinylbenzyl chloride 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 154230-29-2 (E)-4-chlorostyrylboronic acid 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 104-03-0 4-nitrobenzeneacetic acid 
• 1615-02-7 p-chlorocinnamic acid 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 15851-77-1 {4-[(4-chlorophenyl)ethynyl]phenyl}amine 
• 14064-70-1 (Z)-(4-chlorophenyl)(4'-nitrophenyl)ethene 
• 15852-01-4 1-chloro-4-[(4-nitrophenyl)ethynyl]benzene 
• 168151-97-1 N-[4-(4-Chloro-phenylethynyl)-phenyl]-2-cyano-acetamide 
• 168151-99-3 (Z)-(4-aminophenyl)(4'-chlorophenyl)ethene 
• 168151-98-2 N-{4-[(Z)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-2-cyano-acetamide 
• 15948-51-3 1-(4-chlorophenyl)-1,2-dibromo-2-(4'-nitrophenyl)ethane 
• 7389-19-7 (E)-(4-aminophenyl)(4'-chlorophenyl)ethene 
• 15948-51-3 meso-p-chloro-p'-nitrostilbene dibromide 

Relevant academic research and scientific papers

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.

NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media

The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is

Palladium anchored on guanidine-terminated magnetic dendrimer (G3-Gu-Pd): An efficient nano-sized catalyst for phosphorous-free Mizoroki-Heck and copper-free Sonogashira couplings in water

In this research, a novel type of Fe3O4&at;silica-supported dendrimer capped by guanidine groups for immobilization of palladium was reported. This novel nano-sized catalyst was characterized by FTIR, TGA, XRD, FESEM, EDX, VSM, XPS and HRTEM methods. Enhanced catalytic activity of the prepared catalyst in Mizoroki-Heck and copper-free Sonogashira coupling reactions were evaluated in water as a green solvent. The influence of the various reaction parameters such as catalyst dosage, time and temperature on two mentioned C–C coupling reactions were studied. Results showed that the catalyst could be easily recovered by simple separation by an external magnet and reused for five cycles of recovery without considerable losing of its activity.

Diarylethene synthesis method without transition metal catalysis

The invention discloses a diarylethene synthesis method without transition metal catalysis. The method comprises the following steps: a cinnamic acid derivative and aryl trifluoroborate are subjectedto a decarboxylation coupling reaction in a solvent under the action of an oxidizing agent, postprocessing is performed after the reaction, and diarylethene is obtained. K2S2O8 is adopted to promote acatalytic system in the synthetic method, and a free radical coupling reaction can be performed directly under the condition that no ligand, transition metal or alkali is added. The method has widersubstrate range and higher yield; the method is simple to operate, reaction conditions are mild, and large-scale application is facilitated.

Preparation method of palladium catalyzed 1,2-trans diaryl alkene

The invention discloses a preparation method of palladium catalyzed 1,2-trans diaryl alkene. The method comprises the following steps that under the effects of catalysts, cocatalysts and alkali, arylacrylic acid and aromatic esters p-toluene sulfonate take decarboxylation coupling reaction in an organic solvent; after the reaction is finished, the 1,2-trans diaryl alkene is obtained through posttreatment. The method has the advantages that through C-O bond fracture, the operation is simple; a stable palladium catalyst with low cost is used; the substrate applicability is high; the harsh reaction conditions and the addition of strong alkali are not needed; the trans 1,2-diaryl alkene can be generated at high selectivity.

First Cp*Co(III)-catalyzed Mizoroki-Heck coupling reactions of alkenes and aryl bromide/iodide

A Cp*Co(CO)I2 catalyzed Mizoroki-Heck coupling of alkenes and aryl halide is established at feasible reaction conditions. The Cp*Co(III) catalyst excellently work to couple the aryl iodide and alkene, and produce up to 94% yield of the coupling

Palladium-catalyzed decarboxylative coupling of α,β-unsaturated carboxylic acids with aryl tosylates

We report a general method for selective cross-coupling of α,β-unsaturated carboxylic acids with aryl tosylates enabled by versatile Pd(II) complexes. This method features the general cross-coupling of ubiquitous α,β-unsaturated carboxylic acids by decarboxylation. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Pd(II) catalysts, scalability and wide substrate scope. The reaction proceeds with high trans selectivity to furnish valuable (E)-1,2-diarylethenes.

Phosphanamine-functionalized magnetic nanoparticles (PAFMNP): An efficient magnetic recyclable ligand for the Pd-catalyzed Heck reaction of chloroarenes

A phosphanamine-functionalized trimethoxysilyl compound (DPPPA) was synthesized and reacted with magnetic nanoparticles in order to synthesise a novel magnetic reusable phosphanamine ligand (PAFMNP) for application in transition metal-catalyzed coupling reactions. The Pd complex of PAFMNP (Pd-PAFMNP) was found to be an efficient heterogeneous catalyst for the Heck reaction of aryl chlorides. Only 1.0 mol% of catalyst was needed to accomplish the Heck reaction of the aryl chlorides. The catalyst was reusable at least 5 times without a significant decrease in its catalytic activity.

Synthesis of new surfactant-like triazine-functionalized ligands for Pd-catalyzed Heck and Sonogashira reactions in water

In this study, a novel class of ligands for palladium-catalyzed C-C coupling reactions in water is introduced. A range of triazine-functionalized ligands were synthesized using 2,4,6-trichloro-1,3,5-triazine (TCT) reagent. Among them, N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) was found to be an efficient ligand for the Pd-catalyzed Heck and Sonogashira reactions in water, which acted as a green solvent. TEM analysis showed that in the presence of TDTAT in water at 80°C, PdCl2 is converted to nanoparticles with an average size of ～3 nm. The formed Pd-nanoparticles act as efficient catalytic species for C-C bond formation reactions in neat water. Under these conditions, Pd-catalyzed Heck and Sonogashira reactions are accomplished without the need for phosphine ligand. The generation of emulsion droplets (5-10 μm) containing Pd(0) nanoparticles would function as an effective reactor to accelerate the rate of the reaction in water media.

Pd(II) complexes with amide-based macrocycles: Syntheses, properties and applications in cross-coupling reactions

This work shows Pd(ii) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e--donating and e--withdrawing substituents on the ligand framework. Ligands constitute a N4 square-planar cavity and optimally house the Pd(ii) ion. The solution-state structure via NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands.