130059-91-5

Upstream product

• 99429-99-9 4-methylphenyl cinnamate 
• 20498-63-9 1-(4-methylphenyl)-2-phenylethanol 
• 19019-27-3 phenyl-4-methylphenylbenzaldehyde azine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 106-49-0 p-toluidine 
• 2001-28-7 2-phenyl-1-p-tolyl-ethanone 
• 100-42-5 styrene 
• 60126-95-6 p-tolylazoxy p-tolyl sulphone 
• 10557-67-2 N-nitroso-p-methyl-acetanilide 
• 33604-67-0 (4-methylphenyl)azo 4-methylphenyl sulfone 
• 60126-94-5 phenylazoxy p-tolyl sulphone 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1657-45-0 (Z)-4-methylstilbene 
• 14310-20-4 4-methylbibenzyl 
• 102009-55-2 diethyl-(4-trans-styryl-benzyl)-amine 
• 110050-03-8 dipropyl-(4-trans-styryl-benzyl)-amine 
• 10516-47-9 bis-(2-hydroxy-ethyl)-(4-trans-styryl-benzyl)-amine 
• 100461-32-3 meso-4-methylstilbene dibromide 
• 74614-35-0 α-methoxy-4'-methyl-deoxybenzoin oxime 
• 16726-79-7 trans-1-(4-Phenyl-styryl)-4-stryl-benzol 
• 6194-48-5 Phenyl-β-naphthyldivinylbenzene (P-β-NDVβ) 
• 70151-74-5 4-styrylbenzyl bromide 
• 24601-55-6 ethyl trans-2-(4-methylphenyl)-3-phenylcyclopropanecarboxylate 
• 72301-55-4 2-Fluoro-1-phenyl-2-p-tolyl-ethanol 
• 72301-53-2 2-Fluoro-2-phenyl-1-p-tolyl-ethanol 
• 72301-52-1 2-Fluoro-2-phenyl-1-p-tolyl-ethanol 

Relevant academic research and scientific papers

Nickel nanoparticles supported on diphenylphosphinated poly(vinyl alcohol-co-ethylene) as a new heterogeneous and recyclable catalyst for Mizoroki–Heck reactions

Nickel nanoparticles (NiNPs) supported on diphenylphosphinated poly(vinyl alcohol-co-ethylene) (DPP-PVA-co-PE) were synthesised by first reacting poly(vinyl alcohol-co-ethylene) with chlorodiphenylphosphine (ClPPh2) under basic conditions and then treating the product with Ni(OAc)2 followed by reduction with NaBH4. (DPP-PVA-co-PE)-NiNPs, a new metallised polymer, was then shown to efficiently catalyse Mizoroki–Heck reactions of aryl iodides, bromides or activated chlorides with olefins such as styrene and n-butyl acrylate in dimethylformamide. In contrast with other polymer-supported catalysts, the main advantage of this method is the low cost of the catalyst due to the simple synthetic route using easily obtained materials and good recoverability. Transmission electron microscopy and X-ray diffraction measurements were used to show the high metal dispersion and small sizes of Ni nanoparticle on the surface of the modified polymer. DPP-PVA-co-PE-NiNPs could be recycled several times.

Nanoporous hypercrosslinked polymers containing Tg enhancing comonomers

Hypercrosslinked polymers containing functionalized alternating copolymer sequences of substituted stilbene or styrene and N-aryl substituted maleimides have been synthesized. Alternating copolymers containing these comonomers possess semi-rigid structures, and incorporation of these units into the precursor polymer particles for hypercrosslinking leads to a systematic increase in Tg and chain stiffness of these materials as the concentration of the comonomers is increased. Surface area and porosity of the subsequent hypercrosslinked polymers were investigated using nitrogen adsorption/desorption isotherms at 77 K. These hypercrosslinked polymers exhibit BET surface areas ranging from 1058 m2/g at 25 mol% alternating copolymer incorporation down to loss of measurable surface area at ca. 60% incorporation. The experimental surface area results correlate with predictions from simulations and serve as model systems for future studies on specifically functionalized hypercrosslinked polymer particles.

Three phase microemulsion/sol-gel system for aqueous C-C coupling of hydrophobic substrates

Heck, Stille, Suzuki and three-component coupling reactions with hydrophobic substrates have been carried out in water. The substrates are initially transformed by a general procedure into a microemulsion, which consists of nearly 90% water with the aid of sodium dodecyl sulfate and either PrOH or BuOH. The surfactant carries the molecules of the substrates to Pd(OAc)2 entrapped within a hydrophobicitized silica sol-gel matrix where the coupling between the substrates is assumed to take place. The products are then returned by the surfactant into the microemulsion from which it can be released. The immobilized palladium catalyst is leach proof and recyclable. It can be used in various coupling processes at least six times without loss of activity. Experiments with D2O have revealed that the water does not take part in the coupling process, but it has an effect on the pore size of the sol-gel matrix, which hosts the palladium catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes

Arene and phenylmethanesulfonyl chlorides can be cross-coupled with aryl, heteroaryl, and alkenylstannanes with desulfitation in the presence of 10 mol % CuBr·Me2S, 1.5 mol % Pd2dba3, and 5 mol % tri-2-furylphosphine in tetrahydrofuran or toluene under reflux. This extension of the Stille cross-coupling reaction realizes a new and economical method for the generation of C?C bonds. The palladium-catalyzed carbonylative Stille cross-coupling reactions of arenesulfonyl chlorides and organostannanes in the presence of CO (60 bar) at 110 °C in toluene generate the corresponding ketones. Arenesulfonyl chlorides are more reactive than aryl chlorides and aryl bromides in their Stille cross-coupling with organostannanes but less reactive than aryl iodides. The new methods disclosed for the generation of C?C bonds open new possibilities for medicinal chemistry and material sciences. Copyright

Palladium-EDTA and palladium-EdteH4 catalyzed Heck coupling reactions in pure water

Palladium-catalyzed Heck coupling reactions of styrene with bromoarene derivatives are carried out under aerobic conditions in water using water-soluble N;N;N ′ ;N ′ -tetrakis(2-hydroxyethyl)ethylenediamine (EdteH4) and ethylenediaminetetraacetic acid dis

In situ generation of highly active dissolved palladium species from solid catalysts - A concept for the activation of aryl chlorides in the heck reaction

Needing a leach: Optimized palladium/metal oxide systems are highly active heterogeneous catalysts for the Heck reaction. Non-activated and deactivated aryl chlorides can be converted by palladium/zeolite (NaY) catalysts (see scheme). The dissolution of palladium (leaching) from the surface of the support, its redeposition, and the control of these equilibria are found to be crucial for the success of the reaction.

Bimetallic nano alloy architecture on a special polymer: Ni or Cu merged with Pd for the promotion of the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling

Abstract: Novel Ni-Pd and Cu-Pd bimetallic nano alloys was designed and heterogenized on the highly robust ABPBI [poly(2,5-benzimidazole)] polymer in high yields using NaBH4 as reducing agent. These were versatile ligand free catalysts for the Mizoroki–Heck reaction and Suzuki–Miyaura coupling. The bimetallic Ni-Pd-ABPBI catalyst for the Mizoroki–Heck reaction of 4-iodo anisole could be recycled 5 times with high yields. Aryl bromides could also be activated for the Mizoroki–Heck reaction using Cu-Pd-ABPBI NP catalysts, with moderate yields. Graphic abstract: Synopsis Novel bimetallic Ni-Pd and Cu-Pd nano alloys, heterogenized on the robust ABPBI [poly(2,5-benzimidazole)] polymer using NaBH4 as reducing agent, is described. These were versatile ligand free, noble metal conservative catalysts, for the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling. Aryl bromides were activated for the Mizoroki–Heck reaction using the Cu-Pd-ABPBI catalyst.[Figure not available: see fulltext.]

Palladium complexes with hydrophosphorane ligands (HP～O and HP～N), catalysts for Heck cross-coupling reactions

The synthesis and structural characterization of palladium complexes 1-3 incorporating H-spirophosphorane HP(OCMe2CMe2O) 2 and H-phosphonate congener HP(O)(OCMe2CMe2O) ligands are reported. The chemical composition of the complexes [PdCl(μ-Cl){P(OCMe2CMe2O)OCMe2CMe 2OH}]2 (1), [Pd{P(O)(OCMe2CMe 2O)}2]n (2), and [Pd(μ-Cl){P(OCMe 2CMe2O)OH}{P(OCMe2CMe2O)O}] 2 (3) was established by means of NMR, IR, ESI-MS spectroscopic methods. The relative stereochemistry of 1 and 3 was unambiguously determined by single X-ray diffraction studies. It was proved that complexes 1-3, and complex [PdCl2P(OCH2CMe2NH)OCH2CMe 2NH2] (4) previously described in the literature, are very efficient catalysts for the Heck cross-coupling of bromobenzene with n-butyl acrylate. Moreover, they were also found to be effective catalysts in the stereoselective synthesis of trans-stilbenes.

Removal of benzotriazole moiety from 2-[2-aryl-2-(benzotriazol-1- yl)ethyl]tetrahydro-2H-pyrans and 2-[2-aryl-2-(benzotriazol-1-yl)ethyl]-5- (methyl)tetrahydrofurans using lithium naphthalene radical anion

In order to see the effects of non-bonding electrons in oxygen atoms on the cleavage of a bond between N-1 of the benzotriazole moiety and the a- carbon atom bonded to N-1 by lithium (6a) and sodium naphthalenides (6b), 2- [2-aryl-2-(benzotriazol-1-yl)ethyl]tetrahydro-2H-pyrans (4), and 2-[2-aryl- 2-(benzotriazol-1-yl)ethyl]-5-(methyl)tetrahydrofurans (5), and 1- (benzotriazol-1-yl)-1,2-diphenylethane (7) were prepared. The reactions of 4 with 6a in THF at room temperature gave 2-(2-arylethyl)tetrahydro-2H-pyrans (12) in 45 to 62 % yields along with benzotriazole and naphthalene. In addition, 2-(benzoylethyl)tetrahydro-2H-pyran (15) (12 %) was obtained only from the reaction of 2-[2(benzotriazol-1-yl)-2-(phenyl)ethyl]tetrahydro-2H- pyran. Similarly, the reactions of 5 with 6a under the same conditions afforded 2-(2-arylethyl)-5-(methyl)tetrahydrofurans (30) in 59 to 77 % yields along with the foregoing byproducts. Interestingly, the reaction of 7 with 6a under the same conditions gave deoxybenzoin (24) in 41% yield along with the foregoing byproducts. The results suggest that 6a acts as a single electron- transfer agent in the reactions of 4 and 5, and a base in the reaction ofT. It is envisaged that for the former, Li+ participates in the formation of a six-membered cyclic intermediate so that cleavage of a-C-N-1 bond is facilitated to give eventually 12 and 22, whereas for the latter, 6a abstracts a proton from a-C bonded to N-1 to generate a carbanion 19, which extrudes a nitrogen molecule to generate a new phenyl carbanion 20. Protonation leading to mono iminobenzoin 21, followed by hydrolysis gives 15. The formation of 24 can be explained based on the same mechanism as for the latter reaction.

Silicone as a new class of organosilicon reagent for the palladium-catalyzed cross-coupling reaction

Silicone, polyorganosiloxane, serves as an organosilicon reagent for palladium-catalyzed cross-coupling reactions. Treatment of polymethylphenylsiloxane, poly(alkenyl)methylsiloxane, or cyclic oligosiloxanes with various aryl iodides in the presence of silver(I) oxide or tetrabutylammonium fluoride and a catalytic amount of Pd(0) affords the corresponding coupling product in a good to excellent yield.