20488-43-1

Upstream product

• 100-42-5 styrene 
• 99-90-1 para-bromoacetophenone 
• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 
• 92074-28-7 1-phenyl-1-(tributylstannyl)ethene 
• 99-91-2 para-chloroacetophenone 
• 65119-09-7 1-styryltriethoxysilane 
• 134837-65-3 1-octenyltriethoxysilane 
• 1942-31-0 4-(phenylethinyl)acetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 536-74-3 phenylacetylene 
• 3457-45-2 p-formylacetophenone 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 100-39-0 benzyl bromide 
• 99-92-3 p-aminobenzophenone 

Downstream Products

• 72301-36-1 threo-1-fluoro-2-(trifluoroacetoxy)-1-(4-acetophenyl)-2-phenylethane 
• 101168-77-8 (E)-1-(4-styrylphenyl)ethan-1-ol 
• 1429521-53-8 (E)-phenyl 2-(1-(4-styrylphenyl)ethylidene)hydrazinecarboxylate 
• 32555-96-7 4-styrylbenzaldehyde 
• 330442-12-1 1‐(4‐acetylphenyl)‐2‐phenylethan‐1,2‐dione 
• 72301-37-2 1-[4-(1-Fluoro-2-hydroxy-2-phenyl-ethyl)-phenyl]-ethanone 
• 6928-98-9 (E)-1-(1-(tert-butylperoxy)-3,3,3-trifluoropropyl)-4-styrylbenzene 

Relevant academic research and scientific papers

Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki-Miyaura reactions in aqueous media

Representative cross-coupling reactions of aryl bromides with different types of aryl-, alkyl, trivinylboroxine-pyridine complex, and alkenylboronic acids are performed using a polymer-bonded palladacycle derived from Kaiser oxime resin as precatalyst and

Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes

Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes was developed, using a simple nickel foam as catalyst and H3O+ or D3O+ as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.

A Solid-Phase Assisted Flow Approach to In Situ Wittig-Type Olefination Coupling

Described herein is the development of a continuous flow, solid-phase triphenylphosphine (PS-PPh3) assisted protocol to facilitate the in situ coupling of reciprocal pairs of halogen and carbonyl functionalised molecular pairs by a Wittig olefination within 15 mins. The protocol entails injecting a single solution (1 : 1 CHCl3 : EtOH) containing the halogenated and carbonyl-based substrates into a continuously flowing stream of CHCl3 : EtOH (1 : 1), passed through a fixed bed of K2CO3 and PS-PPh3. With advancement to the previous PS-PPh3 coupling procedures, the method employs a traditional polystyrene-based immobilisation matrix, the substrate scope of the protocol extended to substituted ketones, secondary alkyl chlorides, and an unprotected maleimide scaffold.

Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides

Mononuclear and tetranuclear palladium complexes with functionalized "abnormal"N-heterocyclic carbene (aNHC) ligands based on 3-phenylimidazo[1,5-a]pyridine were synthesized. All of the new complexes were structurally characterized by single-crystal X-ray diffraction studies. The new complexes were applied in the Mizoroki-Heck coupling reaction of aryl chlorides with alkenes in neat n-tetrabutylammonium bromide (TBAB). The mononuclear palladium complex with a tridentate phenoxy- and amidate-functionalized aNHC ligand displayed activity superior to that of the palladium complex with a bidentate amidate-functionalized aNHC ligand. The new tetranuclear complex with the tridentate ligand displayed the best activities, capable of the activation of deactivated aryl chlorides as substrates with a low Pd atom loading. Even challenging sterically demanding ortho-substituted aryl chlorides were successfully utilized as substrates. The studies revealed that the robustness of the catalyst precursor is crucial in delivering high catalytic activities. Also, the promising use of tetranuclear palladium complexes with functionalized aNHC ligands as the catalyst precursors in the Mizoroki-Heck coupling reaction in neat TBAB was demonstrated.

Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone

Herein we report a simple protocol for the valorisation of a common urban biowaste. The lignocellulosic biomass obtained after the pre-treatment of pine needle urban waste is efficiently transformed into a low-cost support (PiNe) for the immobilization of Pd nanoparticles. The final Pd/PiNe heterogeneous catalyst features a small particle size (4.5 nm) and a metal loading (9.9 wt%) comparable with most commercially available and generally used counterparts. In this contribution, we tested the catalytic efficiency of the Pd/PiNe system in two representative cross-couplings, Heck and Hiyama reactions, and compared the results obtained with commercial Pd/C catalyst. The good reactivity in the biomass-derived solvent (GVL) confirms that the Pd/PiNe heterogeneous catalyst is a valid system that can be integrated into a waste valorization chain within a circular economy approach. In addition, the efficiency of the catalyst has also been extended to perform the challenging consecutive Hiyama-Heck reaction to afford differently substituted (E)-1,2-diarylethenes.

Mizoroki-Heck carbon-carbon cross-coupling reactions by water-soluble palladium (II) complexes in neat water

Water-soluble palladium complexes were synthesized, characterized, tested as (pre)catalyst for Mizoroki-Heck carbon-carbon cross-coupling reactions in water. Cross-coupling of aryl iodides and bromides with methyl and ethyl acrylates was achieved at 140 °

Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent

Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.

Palladium Nanoparticles Anchored on Magnesium Organosilicate: An Effective and Selective Catalyst for the Heck Reaction

A new and effective palladium catalyst supported on a magnesium organosilicate for application in the Heck reaction is presented. A group of compounds comprising 22 examples were synthesized in moderate to high yields (up to 99%) within a short time. The palladium supported on magnesium organosilicate catalyst was characterized as an amorphous solid by SEM, containing around 33% of palladium inside the solid, and even with this low quantity of palladium, the catalyst was very efficient in the Heck reaction. Besides, based on the Scherrer equation, the crystallite size of the synthesized palladium nanoparticles was ultrasmall (around 1.3 nm). This strategy is a simple and efficient route for the formation of C-C bonds via the Heck cross-coupling reaction.

Palladium Loaded Dendronized Polymer as Efficient Polymeric Sustainable Catalyst for Heck Coupling Reaction

The palladium incorporated amine-functionalized dendronized polymer was synthesized by the addition of palladium acetate to dendronized polymer in methanol at room temperature. Palladium species are immobilized onto the dendritic structure by their coordination with amino functional groups. The newly developed dendritic system showed high palladium content in the low generation level itself, which was found to be 4.19?mmol/g. This was fairly higher than, the other palladium-based catalysts. Energy dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, UV–Visible spectroscopy, and X-ray photoelectron spectroscopy were used to confirm the successful synthesis of the new catalyst. It was used as a homogeneous palladium catalyst for Heck coupling reaction between olefins and differently substituted aryl halides and the products were isolated in high yield. The products isolated were in trans configuration, which indicated the selectivity of the newly developed catalytic system. Also, this catalyst system was reused up to nine times without a significant decrease in its catalytic activity. The easy accessibility of catalytic sites, stability, resistance to metal leaching, high catalytic activity and remarkable stereoselectivity with a low amount of catalyst are all due to the dendritic support. The docking study was carried out for all the stilbene derivatives obtained by the Heck coupling reaction against DprE1 protein to study its potential antitubercular activity. All the compounds displayed superior docking score values over the range ??6.5 to ??8.2?kcal/mol, compared to the standard drug isoniazid with docking score of ??6.1?kcal/mol against DprE1. Graphic Abstract: [Figure not available: see fulltext.]

Copper(0) nanoparticle catalyzed Z-Selective Transfer Semihydrogenation of Internal Alkynes

The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead-free alternative to Lindlar catalysts. A stereo-selective methodology for the hydrogenation of internal alkynes to the corresponding (Z)-alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non-noble copper nanoparticles for reduction of both electron-rich and electron-deficient, aliphatic-substituted and aromatic- substituted internal alkynes. Polyols, such as ethylene glycol and glycerol, have been proven to act as hydrogen sources, and excellent stereo- and chemoselectivity have been observed. Enabling technologies, such as microwave and ultrasound irradiation are shown to enhance heat and mass transfer, whether used alone or in combination, resulting in a decrease in reaction time from hours to minutes. (Figure presented.).