34480-00-7

Upstream product

• 29559-27-1 1-methyl-4-(nitromethyl)benzene 
• 589-18-4 4-Methylbenzyl alcohol 
• 106-42-3 para-xylene 
• 4413-31-4 Methylchlor 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 4702-76-5 4,4'-dimethylbenzaldazine 
• 6749-78-6 4-methylphenylmagnesium iodide 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 20710-51-4 4,4'-Dimethyl-bis-thiobenzoyldisulfid 
• 51419-59-1 4-methylbenzylsulfonyl chloride 
• 2378-86-1 4-methylbenzyltriphenylphosphonium bromide 
• 104-87-0 4-methyl-benzaldehyde 
• 35779-32-9 1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene 

Downstream Products

• 1576-67-6 3,6-dimethylphenanthrene 
• 3719-84-4 2,3-bis(4-methylphenyl)quinoxaline 
• 162407-11-6 2,3-di-p-tolyl-1,4-diazaspiro[4.5]deca-1,3-diene 
• 3457-48-5 1,2-di(4-methylphenyl)-1,2-ethanedione 
• 120336-96-1 N-<(4-Methylphenyl)sulfonyl>-4-methylbenzenecarboxamide 
• 75159-10-3 N-(4-methylbenzylidene)-p-toluenesulfonamide 
• 104-87-0 4-methyl-benzaldehyde 
• 1588-49-4 trans-4,4'-dimethylstilbene radical cation 
• 101111-08-4 4-methyl 4'-bromomethyl stilbene 
• 60682-97-5 4,4'-bis(bromomethyl)stilbene 
• 23843-15-4 4,4'-trans-(4-Isopropyl-styryl)-trans-stilben 
• 1017137-39-1 (±)-2,3-bis(4-methylphenyl)propanoic acid 

Relevant academic research and scientific papers

Synthesis and Catalytic Applications of [N,N]-Pyrrole Ligands for the Regioselective Synthesis of Styrene Derivatives

We report the synthesis of two [N,N]-donor ligands (5 a–b) containing a 2-chalcogenazoline as the structural motif. These compounds were synthesized from a common intermediate Fischer type aminocarbene complex (3). The palladium-complexes of these [N,N]-donor ligands were successfully used as catalytic precursors in the Mizoroki-Heck coupling reaction between aryl halides and methyl acrylate, styrene and ethylene. For methyl acrylates, high yields with TOF values between 0.6 and 5.5×105 h?1 were obtained. In the case of ethylene, we reached high regioselectivities to obtain a diversity of styrene derivatives under soft pressure conditions, with good values of TON and TOF. (Figure presented.).

Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions

A series of three 1,3-propanediyl bridged bis(N-heterocyclic carbene)palladium(II) complexes (Pd-BNH1, Pd-BNH2, and Pd-BNH3), with + I effect order of the N-substituents of the ligand (isopropyl > benzyl > methoxyphenyl), was the subject of a spectroscopic, structural, computational and catalytic investigation. The bis(NHC)PdBr2 complexes were evaluated in Mizoroki-Heck coupling reactions of aryl bromides with styrene or acrylate derivatives and showed high catalytic efficiency to produce diarylethenes and cinnamic acid derivatives. The X-ray structure of the most active palladium complex Pd-BNH3 shows that the Pd(II) center is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromide ligands in cis position, resulting in a distorted square planar geometry. The NMR data of Pd-BNH3 are consistent with a single chair-boat rigid conformer in solution with no dynamic behavior of the 8-membered ring palladacycle in the temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated softness, in the case of Pd-BNH3, is expected to favor the coordination steps of both the soft aryl bromides and alkenes in the Heck catalytic cycle.

Palladium nanoparticlesin situsynthesized onCyclea barbatapectin as a heterogeneous catalyst for Heck coupling in water, the reduction of nitrophenols and alkynes

This study develops an effective method for thein situsynthesis of palladium nanoparticles (PdNPs) usingCyclea barbatapectin as a green reducing and stabilizing reagent. The PdNP@pectin nanocomposite was well characterized by analysis techniques such as UV-vis, FTIR, EDX, XRD, SEM, HR-TEM and STEM-mapping. Crystalline PdNPs were found to be distributed in the size range of 1-25 nm with the highest frequency of 6-12 nm. PdNP@pectin exhibited excellent recyclable catalysis activity for the Heck coupling reaction in water medium. The kinetics and recyclability of nanoparticles were investigated for the catalytic reduction ofo-,m- andp-nitrophenol. The result showed a good catalysis efficiency with five successful recycles without compromising much. In particular, the nanocomposite was used as a catalyst for the conversion of alkynes intocis-alkenes with KOH/DMF as a hydrogenation source. The reaction was also utilized effectively for the synthesis of sex pheromones, includingPlutella xylostella((Z)-11-hexadecen-1-yl acetate) andCylas formicarius((Z)-3-dodecen-1-yl(E)-2-butenoate) with the total yields of 70% and 68%, respectively. Therefore, PdNPs supported onC. barbatapectin are promising catalysis materials for application in various fields.

Porous organic polymer supported rhodium as a heterogeneous catalyst for hydroformylation of alkynes to α,β-unsaturated aldehydes

A new porous organic polymer supported rhodium catalyst (Rh/POL-BINAPa&PPh3) has been developed for the hydroformylation of various alkynes to afford the corresponding α,β-unsaturated aldehydes with high chem- and stereoselectivity, excellent catalytic activity and good reusability (10 cycles). The heterogeneous catalyst exhibited more catalytic activity than the comparable homogeneous Rh/BINAPa/PPh3 system.

Synthesis of [7]Helicene Enantiomers and Exploratory Study of Their Conversion into Helically Chiral Iodoarenes and Iodanes

The facile and convenient preparation of both enantiomers of a [7]helicene scaffold from inexpensive (l)-(+)-tartaric acid and 4-methylstyrene is described. These helical structures were transformed into bis-iodinated ether derivatives in order to explore their potential as precursors of novel chiral organoiodane reagents or as iodoarene pre-catalysts. Promising results were obtained in hydroxylative phenol dearomatization/[4+2] cycloaddition cascade and dearomative spirolactonization reactions with encouraging enantiomeric excesses.

Immobilized Pd on (S)-methyl histidinate-modified multi-walled carbon nanotubes: A powerful and recyclable catalyst for Mizoroki-Heck and Suzuki-Miyaura C-C cross-coupling reactions in green solvents and under mild conditions

A stable and powerful heterogeneous palladium catalyst was synthesized using immobilized palladium on (S)-methyl histidinate bonded onto the surface of multi-walled carbon nanotubes. The catalyst was characterized using a combination of Fourier transform infrared and X-ray photoelectron spectroscopies, transmission electron microscopy, X-ray powder diffraction and inductively coupled plasma, thermogravimetric and elemental analyses. This new air- and moisture-stable phosphine-free palladium catalyst was found to be highly active and reusable in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions in poly(ethylene glycol) and aqueous ethanol as green solvents using an extremely small amount of palladium under mild conditions.

Metal-catalyzed formal amidation of alkenes under CO-free condition

An effective procedure for synthesis of amides from alkenes and [Formula presented] via Pd and Fe catalysts under mild conditions is described. A series of benzamides containing various functional groups can be obtained in reasonable yield and the possible reaction pathway is proposed in this Letter.

Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: Efficient access to α-alkyl vinylarenes

Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA)2/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 °C under 1 atm of O2 without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.

Biomimetic oxidative dimerization of anodically generated stilbene radical cations: Effect of aromatic substitution on product distribution and reaction pathways

A systematic study of the electrochemical oxidation of 1,2-diarylalkenes was carried out with the focus on detailed product studies and variation of product type as a function of aromatic substitution. A reinvestigation of the electrochemical oxidation of 4,4′-dimethoxystilbene under various conditions was first carried out, and all products formed were fully characterized and quantitated. This was followed by a systematic investigation of the effect of aromatic substitution on the nature and distribution of the products. The aromatic substituents were found to fall into three main categories, viz., substrates in which the nature and position of the aromatic substituents gave rise to essentially the same products as 4,4′- dimethoxystilbene, for example, tetraaryltetrahydrofurans, dehydrotetralins, and aldehydes (p-MeO or p-NMe2 on one ring and X on the other ring, where X = o-MeO or p-alkyl, or m- or p-EWG; e.g., 4-methoxy-4′- trifluoromethylstilbene); those that gave rise to a mixture of indanyl (or tetralinyl) acetamides and dehydrotetralins (or pallidols) (both or one ring substituted by alkyl groups, e.g., 4,4′-dimethylstilbene); and those where strategic placement of donor groups, such as OMe and OH, led to the formation of ampelopsin F and pallidol-type carbon skeletons (e.g., 4,3′,4′- trimethoxystilbene). Reaction pathways to rationalize the formation of the different products are presented.

Ultrasound-assisted C-C coupling reactions catalyzed by unique SPION-A-Pd(EDTA) as a robust nanocatalyst

A novel and highly stable Pd(EDTA)2- salt was synthesized as a catalyst, using a counter-cation of N-methylimidazolium bonded to 1,3,5-triazine-tethered SPIONs (superparamagnetic iron oxide nanoparticles). This well-defined complex efficiently