38112-01-5

Upstream product

• 95-47-6 o-xylene 
• 98-88-4 benzoyl chloride 
• 1220985-64-7 (E)-N'-(1-(3,4-dimethylphenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 98-80-6 phenylboronic acid 
• 615-60-1 4-chloro-1,2-dimethylbenzene 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 536-74-3 phenylacetylene 
• 2571-39-3 (3,4-dimethylphenyl)(phenyl)methanone 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 6196-95-8 1,2-dimethyl-4-(1-phenylethyl)benzene 
• 2571-39-3 (3,4-dimethylphenyl)(phenyl)methanone 

Relevant academic research and scientific papers

TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclicN,O-acetals

A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins2a,2fand2gwith imines1a-1g, and a series of aryl substituted skipped dienes3aa-3gfwere accordingly obtained in 62%-94% yields. Moreov

Halogenation of 1,1-diarylethylenes by N-halosuccinimides

An efficient method for the preparation of 2,2-diarylvinyl halides from the corresponding 1,1-diarylethylenes has been developed. N-Halosuccinimides (N-bromosuccinimide or N-chlorosuccinimide) were used as the halogenation reagents. The practicability of this method is highlighted by its simple operation, broad substrate scope and capability for large-scale reaction.

A convenient access to allylic triflones with allenes and triflyl chloride in the presence of (EtO)2P(O)H

A simple method for the preparation of allylic triflones from allenes and triflyl chloride in the presence of (EtO)2P(O)H has been developed. The features of this reaction are catalyst-free and simple starting substrates. This method tolerates diverse functional groups and substituted allylic triflones are obtained in moderate to good yields.

Oxidative [4+2] Cycloaddition of α-(N-Arylamino) Carbonyls with Aryl Alkenes by Multiple C-H Functionalizations and [1,2]-Aryl Shifts

A new, general copper-catalyzed oxidative tandem [4+2] cycloaddition of α-(N-arylamino) carbonyl compounds with aryl alkenes to produce highly substituted quinolines has been developed, which allows the formation of three new C-C bonds through a sequence of multiple C-H functionalizations, annulation, and [1,2]-aryl shifts.

Radical C?H Bond Trifluoromethylation of Alkenes by High-Valent Copper(III) Trifluoromethyl Compounds

A general and selective method is developed that allows direct vinylic C?H bond trifluoromethylation of 1,1-diarylalkenes by a high-valent copper(III) trifluoromethyl complex, producing biologically active trifluoromethylated alkenes (as well as trifluoro

Supported phosphotungstic acid catalyst on mesoporous carbon with bimodal pores: A superior catalyst for Friedel-Crafts alkenylation of aromatics with phenylacetylene

Supported phosphotungstic acid (PTA) catalysts on diverse carriers containing the modified commercially available activated carbon (AC), classical mesoporous carbon via SBA-15 hard template method (CMK-3), and the mesoporous carbon with high surface area and bimodal pores through evaporation-induced tri-constituent co-assembly approach (MC) by using a facile wet impregnation method were employed as solid acid catalysts for Friedel-Crafts alkenylation of p-xylene with phenylacetylene. N2 adsorption–desorption, X-ray diffraction (XRD), and NH3 temperature-programmed desorption (NH3-TPD) characterization techniques were employed to reveal the structure-performance relationship. PTA/MC exhibits much superior catalytic performance to the previously reported PTA/AC, and even to PTA/CMK-3. The PTA/MC catalysts were optimized by varying the PTA loading, and the optimum PTA loading is 35%. The close to 100% of conversion towards phenylacetylene can be achieved in the presence of 2.67% of the 35% PTA/MC solid acid catalyst. It is also found that catalytic properties of the solid acids are strongly depended on acidic properties that affected by the textural properties of supports and PTA loading, as well as the accessibility of active sites affected by specific surface area and pore structure of catalyst. Moreover, the 35?wt.% PTA/MC catalyst has demonstrated outstanding catalytic performance for the Friedel-Crafts alkenylation of diverse aromatics to their corresponding α-arylstyrenes.

Supported phosphotungstic acid catalyst on modified activated carbon for Friedel-Crafts alkenylation of diverse aromatics to their corresponding α-arylstyrenes

Abstract The supported phosphotungstic acid catalysts on modified activated carbon (PTA/AC) prepared by a facile wet impregnation method were employed for Friedel-Crafts alkenylation of diverse aromatics with phenylacetylene to synthesize their corresponding α-arylstyrenes. Reaction results demonstrate that the fabricated PTA/AC catalyst with 30 wt.% PTA loading exhibits outstanding catalytic performance. The 100% conversion of phenylacetylene with 95.7% selectivity towards α-(2,5-dimethylphenyl) styrene can be achieved over the developed 30 wt.% PTA/AC catalyst under optimized reaction conditions, and no visible loss in catalytic performance can be observed after it suffers from several times recycling. The various characterization techniques including X-ray diffraction, N2 adsorption-desorption, Fourier transform infrared spectroscopy, and NH3 temperature-programmed desorption were employed to reveal the relationship between the catalysts nature and catalytic properties. Moreover, the results on the scope of aromatics for the Friedel-Crafts alkenylation illustrate that the developed PTA/AC alkenylation catalyst can be efficiently catalyze the diverse aromatics and even for the electron deficient chlorobenzene. The developed PTA/AC catalyst, using the modified low-cost and sustainable AC as support, may be a robust and promising candidate for highly-efficient and clean α-arylstyrenes production through Friedel-Crafts alkenylation of diverse aromatics including electron-donating and electron-withdrawing groups substituted benzene derivatives as well as heterocyclic and polypolycyclic arenes with phenylacetylene.

Electrophilic Fluorophosphonium Cations in Frustrated Lewis Pair Hydrogen Activation and Catalytic Hydrogenation of Olefins

The combination of phosphorus(V)-based Lewis acids with diaryl amines and diaryl silylamines promotes reversible activation of dihydrogen and can be further exploited in metal-free catalytic olefin hydrogenation. Combined experimental and density functional theory (DFT) studies suggest a frustrated Lewis pair type activation mechanism. FLP hydrogenation: The combination of a phosphorus(V)-based Lewis acid with diaryl amines or diaryl silylamines promotes reversible activation of dihydrogen and can be further exploited in metal-free catalytic olefin hydrogenation. Combined experimental and density functional theory (DFT) studies suggest a frustrated Lewis pair (FLP)-type activation mechanism.

Oxime palladacycle-catalyzed Suzuki-Miyaura alkenylation of aryl, heteroaryl, benzyl, and allyl chlorides under microwave irradiation conditions

A simple new protocol for the palladium-catalyzed Suzuki-Miyaura cross-coupling of organic chlorides under microwave irradiation is presented. Deactivated aryl and heteroaryl chlorides are efficiently cross-coupled with alkenylboronic acids and potassium alkenyltrifluoroborates using the 4,4′-dichlorobenzophenone oxime-derived palladacycle 1b as precatalyst in 0.1 to 0.5 mol% palladium loading, tris(tert-butyl)phosphonium tetrafluoroborate {[HP(t-Bu)3]BF4} as ligand, tetra-n-butylammonium hydroxide as cocatalyst, and potassium carbonate as base in N,N- dimethylformamide at 130°C under microwave irradiation conditions. Under these conditions, styrenes, stilbenes, and alkenylarenes are obtained in good to high yields, and with high regio- and diastereoselectivities in only 20 min. The reported protocol is also very efficient for the regioselective alkenylation of benzyl and allyl chlorides to afford allylarenes and 1,4-dienes. Copyright

Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with arylboronic acids

The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.