132312-99-3

Upstream product

• 637-69-4 4-Methoxystyrene 
• 228873-97-0 hydroxy(dimethyl)(4-trifluoromethylphenyl)silane 
• 40474-01-9 1-methoxy-4-((4-(trifluoromethyl)phenyl)ethynyl)benzene 
• 696-62-8 para-iodoanisole 
• 952739-61-6 (E)-1-(2-iodovinyl)-4-(trifluoromethyl)-benzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 455-13-0 4-Iodobenzotrifluoride 
• 768-60-5 4-methoxyphenylacetylen 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 98-56-6 4-chlorobenzotrifluoride 

Downstream Products

• 40473-97-0 4-Trifluormethyl-4'-methoxy-α,β-dibromstilben 
• 1380439-31-5 (Z)-1-methoxy-4-(1-(p-tolyl)-2-(4-(trifluoromethyl)phenyl)vinyl)benzene 
• 1380439-43-9 (Z)-1-methoxy-4-(2-(p-tolyl)-2-(4-(trifluoromethyl)phenyl)vinyl)benzene 
• 1608492-54-1 (2R,3S,4R,5S)-2,5-bis(4-methoxyphenyl)-3,4-bis(4-(trifluoromethyl)phenyl)tetrahydrofuran 
• 1588534-26-2 C₃₀H₂₀F₆O₂ 
• 40474-01-9 1-methoxy-4-((4-(trifluoromethyl)phenyl)ethynyl)benzene 
• 40474-00-8 4-((4-(trifluoromethyl)phenyl)ethynyl)phenol 

Relevant academic research and scientific papers

Catalytic, Enantioselective syn-Diamination of Alkenes

The enantioselective, vicinal diamination of alkenes represents one of the stereocontrolled additions that remains an outstanding challenge in organic synthesis. A general solution to this problem would enable the efficient and selective preparation of widely useful, enantioenriched diamines for applications in medicinal chemistry and catalysis. In this article, we describe the first enantioselective, syn-diamination of simple alkenes mediated by a chiral, enantioenriched organoselenium catalyst together with a N,N′-bistosyl urea as the bifunctional nucleophile and N-fluorocollidinium tetrafluoroborate as the stoichiometric oxidant. Diaryl, aryl-alkyl, and alkyl-alkyl olefins bearing a variety of substituents are all diaminated in consistently high enantioselectivities but variable yields. The reaction likely proceeds through a Se(II)/Se(IV) redox catalytic cycle reminiscent of the syn-dichlorination reported previously. Furthermore, the syn-stereospecificity of the transformation shows promise for highly enantioselective diaminations of alkenes with no strong steric or electronic bias.

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.

A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol

Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.

Ruthenium-Catalyzed E-Selective Alkyne Semihydrogenation with Alcohols as Hydrogen Donors

Selective direct ruthenium-catalyzed semihydrogenation of diaryl alkynes to the corresponding E-alkenes has been achieved using alcohols as the hydrogen source. The method employs a simple ruthenium catalyst, does not require external ligands, and affords the desired products in > 99% NMR yield in most cases (up to 93% isolated yield). Best results were obtained using benzyl alcohol as the hydrogen donor, although biorenewable alcohols such as furfuryl alcohol could also be applied. In addition, tandem semihydrogenation-alkylation reactions were demonstrated, with potential applications in the synthesis of resveratrol derivatives.

Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes

A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.

An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

An interrupted Pummerer/nickel-catalysed cross-coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one-pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp-, sp2-, and sp3-hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo- and heterocyclic alkenyl sulfonium salts for cross-coupling.

Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI2

An efficient E-selective semihydrogenation of internal alkynes was developed under low dihydrogen pressure and low reaction temperature from commercially available reagents: Cl2Pd(PPh3)2, Zn0, and ZnI2. Kinetic studies and control experiments underline the significant role of ZnI2 in this process under H2 atmosphere, establishing that the transformation involves syn-hydrogenation followed by isomerization. This simple and easy-to-handle system provides a route to E-alkenes under mild conditions.

Selective Semihydrogenation of Alkynes with N-Graphitic-Modified Cobalt Nanoparticles Supported on Silica

For the first time N-graphitic-modified cobalt nanoparticles (Co/phen@SiO2-800) are shown to be active in the semihydrogenation of alkynes to alkenes. Key to success for efficient catalysis is both the modification of the metal nanoparticles by nitrogen-doped graphitic layers and the use of silica as support. Several internal alkynes are converted to the Z isomer in high yields with up to 93% selectivity. In addition, a variety of terminal alkynes, including sensitive functionalized compounds, are readily converted into terminal alkenes. Notably, this non-noble-metal catalyst allows for the purification of alkenes by selective hydrogenation of the corresponding alkyne in the presence of an excess of olefin.

Synthetic method of toluylene compound

The invention relates to a synthetic method of a toluylene compound. According to the reaction, aryl halide or mixed halides and alkene bromine are used as a substrate. Under the action of a catalyst, a ligand, a reducing agent and an additive, the substrate in ice-water bath is slowly heated to room temperature and a mild reaction is carried out for 8-12 h so as to obtain the toluylene compound. The method has advantages of cheap catalyst metal, mild reaction, one-step reaction, simple step, short reaction time, safe operation, high yield, etc.

Direct trans-Selective Ruthenium-Catalyzed Reduction of Alkynes in Two-Chamber Reactors and Continuous Flow

An efficient trans-selective hydrogenation of alkynes under low hydrogen pressure and low reaction temperatures is reported, applying a commercially available ruthenium hydride complex. The developed reaction conditions, which tolerate a variety of functional groups, are carried out in a two-chamber setup with ex situ generated hydrogen. The reaction setup is highly suitable for deuterium labeling. The trans-selective hydrogenation was extrapolated to a transfer hydrogenation protocol, employing a packed bed immobilized ruthenium hydride catalyst in continuous flow with a retention time of only 10 min.