17555-94-1

Upstream product

• 142312-02-5 2-(4-methoxyphenyl)-4-(4-methylphenyl)-5(4H)oxazolone 
• 142087-16-9 1-(4-methylbenzyl)-1H-benzo[d][1,2,3]triazole 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 73839-45-9 (E)-trimethyl[2-(4-methylphenyl)ethenyl]silane 
• 637-69-4 4-Methoxystyrene 
• 17920-15-9 (4-methylphenyl)dimethylsilanol 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 2746-25-0 p-Methoxybenzyl bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 22868-26-4 (p-methoxyphenyl)dimethylsilanol 
• 106-38-7 para-bromotoluene 
• 123-11-5 4-methoxy-benzaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 109441-83-0 (+/-)-threo-4-methoxy-4'-methyl-bibenzyl-α,α'-diol 
• 36707-23-0 1-(4-methylphenyl)-2-(4-methoxyphenyl)ethane 
• 874988-43-9 C₁₆H₁₆Br₂O 
• 18951-45-6 (E)-1-(4-hydroxy)phenyl-2-(4-methyl)phenylethene 
• 17555-94-1 (E)-4'-methoxy-4-methylstilbene 
• 109441-83-0 (+/-)-erythro-4-methoxy-4'-methyl-bibenzyl-α,α'-diol 
• 89902-52-3 2-(4-methoxyphenyl)-2-methoxy-1-(4-methylphenyl)ethanol 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 84857-56-7 4-methoxy 4'-diethoxyphosphonomethyl stilbene 
• 14366-75-7 4-methoxy 4'-bromomethyl stilbene 
• 127066-46-0 1-[2-methoxy-2-(4-methoxyphenyl)ethyl]-4-methylbenzene 
• 54842-60-3 1-methoxy-4-((E)-4-((E)-styryl)styryl)benzene 
• 23798-19-8 trans-1-<4-Phenyl-styryl>-4-<4-methoxy-styryl>-benzol 

Relevant academic research and scientific papers

Transition-Metal-Free Matsuda-Heck Type Cross-Coupling and Mechanistic Evidence for a Radical Mechanism

The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows the selective and direct synthesis of stilbenes from aryldiazonium salts under mild temperature (20 °C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.

Resolution of different conformers of methoxy-trans-stilbenes via rotational coherence spectroscopy

The excitation spectra of 4-methoxy-t-stilbene (MoS) and 4-methoxy,4'-methyl-t-stilbene (MoMeS) both exhibit two electronic origin transitions, separated by 260-280 cm-1.This suggests the presence of two structural forms, as predicted by semi-e

Substituent Effects on Torsional Barriers: p-Methoxy- and p-Methoxy-p'-methyl-trans-stilbene

Jet-cooled fluorescence excitation spectra and selected single vibronic level dispersed fluorescence spectra are presented for p-methoxy-trans-stilbene and p-methoxy-p'-methyl-trans-stilbene.Two stable conformers of the methoxy group are evident in the sp

PVC-NHC-Pd(0): An efficient and reusable heterogeneous catalyst for highly cis-selective semihydrogenation of alkynes using formic acid as hydrogen source

PVC-NHC-Pd(0) catalyst was prepared and exerted to highly cis-selective semihydrogenation of diarylacetylene using formic acid as hydrogen source under mild condition. The as-prepared catalyst was well characterized by various techniques such as FT-IR, 1H NMR, XRD, SEM, EDX, TEM, XPS, and TGA. The catalyst can be easily recovered and recycled without loss of its activity and selectivity owing to the metal-ligand interaction between Pd(0) with polymeric NHC ligands. This protocol is an attractive alternative of the classical Lindlar's hydrogenation.

A photocatalyst-free visible-light-mediated solvent-switchable route to stilbenes/vinyl sulfones from β-nitrostyrenes and arylazo sulfones

Photocatalyst-free visible-light-mediated reactions, based on the presence of a visible-light-absorbing functional group in the starting material itself in order to exclude the often costly, hazardous, degradable and difficult to remove or recover photoredox catalysts, have been gaining momentum recently. We have employed this approach to develop a denitrative photocatalyst-free visible-light-mediated protocol for the arylation/sulfonylation of β-nitrostyrenes employing arylazo sulfones (bench-stable photolabile compounds) in a switchable solvent-controlled manner. Arylazo sulfones served as the aryl and sulfonyl radical precursors under blue LED irradiation for the synthesis oftrans-stilbenes and (E)-vinyl sulfones in CH3CN and dioxane/H2O 2?:?1, respectively. The absence of any metal, photocatalyst and additive; excellent selectivity (E-stereochemistry) and solvent-switchability; and the use of visible light and ambient temperature are the prime assets of the developed method. Moreover, we report the first photocatalyst-free visible light-driven route to synthesize stilbenes and vinyl sulfones from readily available β-nitrostyrenes.

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions

A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.

Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers

Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected C-H alkenylation of aryl ethers promoted by a dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkenylation of alkyl aryl ethers (anisole, phenetole, n-propyl phenyl ether, n-butyl phenyl ether and benzyl phenyl ether), cyclic aryl ethers (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), and diphenyl oxides. Moreover, the proposed methodology was successfully employed for the late-stage modification of complex drugs containing the aryl ether motif. Interestingly, the compounds developed herein displayed fluorescent properties, which would facilitate their biological applications.

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes

A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.