20657-32-3

Upstream product

• 620-19-9 1-chloromethyl-3-methyl-benzene 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 40154-67-4 m-tolyldiazomethane 
• 1711-06-4 3-Methylbenzoyl chloride 
• 620-23-5 m-tolyl aldehyde 
• 2765-16-4 bis(3-methylphenyl)acetylene 
• 35286-92-1 (E)-3,3'-dimethylstilbene 
• 201230-82-2 carbon monoxide 
• 53531-68-3 (3-methylphenyl)methanesulfonyl chloride 

Downstream Products

• 35286-92-1 (E)-3,3'-dimethylstilbene 
• 817160-48-8 cis-2,3-di-m-tolyloxirane 

Relevant academic research and scientific papers

Photocatalyst-free visible light promoted: E → Z isomerization of alkenes

A simple and green method of visible light driven photocatalytic E to Z isomerization of alkenes has been developed. A variety of (Z)-alkenes can be prepared in the presence of visible light, without any additional photocatalyst. This protocol features photocatalyst-free conditions, which are mild, tolerant, and operationally simple, and is easy to implement.

Unsupported Nanoporous Gold Catalyst for Chemoselective Hydrogenation Reactions under Low Pressure: Effect of Residual Silver on the Reaction

For the first time, H-H dissociation on an unsupported nanoporous gold (AuNPore) surface is reported for chemoselective hydrogenation of C=C, C=C, C=N, and C=O bonds under mild conditions (8 atm H2 pressure, 90 °C). Silver doping in AuNPore, which was inevitable for its preparation through a process of dealloying of Au-Ag alloy, exhibited a remarkable difference in catalytic activity between two catalysts, Au>99Ag1NPore and Au90Ag10NPore.The former was more active and the latter less active in H2 hydrogenation, while the reverse tendency was observed for O2 oxidation. This marked contrast between H2 reduction and O2 oxidation is discussed. Further, Au>99Ag1NPore showed a high chemoselectivity toward reduction of terminal alkynes in the presence of internal alkynes which was not achieved using supported gold nanoparticle catalysts and other previously known methods. Reductive amination, which has great significance in synthesis of amines due to its atom-economical nature, was also realized using Au>99Ag1NPore, and the Au>99Ag1NPore/H2 system showed a preference for the reduction of aldehydes in the presence of imines. In addition to this high chemoselectivity, easy recovery and high reusability of AuNPore make it a promising heterogeneous catalyst for hydrogenation reactions.

Immobilization and continuous recycling of photoredox catalysts in ionic liquids for applications in batch reactions and flow systems: Catalytic alkene isomerization by using visible light

A catalytic (E)- to (Z)-isomerization of olefins using a photoredox catalyst under mild reaction conditions is presented. A variety of (Z)-alkenes can be prepared in the presence of visible light. A new reaction system allows an easy and efficient scale-up, as well as a continuous flow process in which the photocatalyst is immobilized in an ionic liquid and continuously recycled by simple phase separation. Catalytic (E)- to (Z)-isomerizations of olefins under mild conditions can be achieved by use of a photosensitizer and visible light. A new reaction system such as depicted allows an easy and efficient scale-up, as well as continuous flow processes in which the photocatalyst is immobilized in an ionic liquid and continuously recycled by phase separation.

Synthesis of a guanidine NHC complex and its application in borylation reactions

Synthesis of guanidine-linked NHC can be achieved easily through reacting amino-NHC with carbodiimide. Subsequently, guanidine-NHC Ag and Cu complexes were isolated and fully characterized. These Cu complexes are found to be versatile catalysts for hydroboration, semihydrogenation and carboboration of alkynes in a highly stereo- and regioselective fashion.

Rhodium-catalyzed hydroformylation of alkynes employing a self-assembling ligand system

Hydroformylation of alkynes is an underdeveloped atom-economic and redox-neutral method to prepare enals. Applying a new electron poor self-assembling ligand system provides the first general rhodium-catalyst for the chemo- and stereoselective hydroformylation of dialkyl- as well as diaryl-substituted alkynes to furnish enals in excellent chemo- and stereoselectivity.

Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex

This study describes a C2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8′-(Hydroxy-diphenyl-methyl)-10,10,10′,10′-tetramethy l-[5,5′]bi[6-aza-tricyclo[7.1.1.02,7/s

REDUCTIVE COUPLING OF BENZOIC ACID HALIDES AND ESTERS USING LOW-VALENT TITANIUM

The reductive coupling of (substituted) benzoic acid chlorides and esters is achieved using low-valent titanium, generated from TiCl3 and LiAlH4.Both acid chlorides and esters seem to follow the same two reaction pathways: one path via tolanes to stilbenes, the other via benzils to complex mixtures of products arising from reduction and further coupling reactions.Although the exact product balance depends upon the reaction conditions the major product is (substituted) cis-stilbene.

Ultrasound-Mediated Synthesis and Mass Spectrometric Fragmentation of Dimethyl-Substituted 1,2-Diphenylethanols, Convenient Dimethylstilbene Precursors

1,2-Diarylethanols were obtained in high yields by ultrasonic irradiation of mixtures of lithium sand, benzylic chlorides, and arenecarbaldehydes or aryl methyl ketones.The mass spectra of the alcohols contained dominant peaks for species formed by dehydration, α-cleavage processes and rearrangement involving hydrogen transfer.Acid-catalyzed dehydration of the alcohols gave the corresponding stilbenes in quantitative yields.

ZEOLITE-CuNaY CATALYZED DECOMPOSITION OF ARYLDIAZOMETHANE

Decomposition of aryldiazomethanes is catalyzed by copper ion-exchanged Y-type zeolite to afford cis-1,2-diarylethylenes in high selectivity.The catalytic activity and selectivity are found to be affected by the exchange level of copper ions in zeolite and the solvent used.

REACTION OF ARYLMETHANESULFONYL AND STYRYLMETHANESULFONYL CHLORIDES WITH TRIETHYLAMINE

A series of arylmethanesulfonyl chlorides were treated with triethylamine in THF to give stilbenes in excellent yields.Workup of the mixtures below 10 deg C permits isolation of stilbene episulfones which on warming decompose to yield the corresponding stilbenes stereospecifically.Application of the reaction to 9-fluorenylsulfonyl chloride affords bifluorenylidene, while trans-styrylmethanesulfonyl chloride gives 4,5-dihydro-4,5-diphenylthiepin 1,1-dioxide and 1,6-diphenylhexatriene.