25144-38-1

Upstream product

• 5328-80-3 2-chlorobenzaldehyde N-[(2-chlorophenyl)methylidene]hydrazone 
• 10577-21-6 1,2-Bis(2-chlorophenyl)-1-chloroethane 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 88-66-4 2-chlorobenzal chloride 
• 77421-13-7 (2-chlorobenzyl)sulfonyl chloride 
• 91110-67-7 1-chloro-2-(phenylsulfonylmethyl)benzene 
• 20657-43-6 (Z)-1,2-bis(2-chlorophenyl)ethene 
• 27872-11-3 2,α,2',α'-tetrachloro-bibenzyl 
• 89-98-5 2-chloro-benzaldehyde 
• 62640-67-9 1-(2'-chlorobenzyl)triphenylphosphonium bromide 
• 1334478-54-4 Br^(1-)*C₂₀H₁₆Cl₂N₃⁽¹⁺⁾ 
• 80447-84-3 (o-chlorobenzyl)methylphenylselenonium tetrafluoroborate 
• 82988-74-7 (2-chlorophenyl)diazomethane 
• 70599-80-3 dl-1,2-Di-o-chlorophenyl-1,2-dinitroethan 

Downstream Products

• 248-70-4 benzthieno[3,2-b]benzothiophene 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 1254175-17-1 2-chloro-2'-mercaptostilbene 
• 1254175-16-0 2-(2-chlorophenyl)-2,3-dihydrobenzo[b]thiophene 
• 257-13-6 dibenzo[b,f]thiepine 
• 20657-43-6 (Z)-1,2-bis(2-chlorophenyl)ethene 
• 1454309-37-5 2-bromo-4-chloro-1-(2-chlorophenyl)-1H-indene 
• 1454309-55-7 2-bromo-7-chloro-3-(2-chlorophenyl)-1H-indene 
• 24133-53-7 (1RS,2RS)-1,2-Bis(2-chlorophenyl)ethane-1,2-diol 
• 27872-11-3 2,α,2',α'-tetrachloro-bibenzyl 

Relevant academic research and scientific papers

Stereoselective synthesis of 1,6-dichloro-1,3,5-hexatriene derivatives by McMurry coupling of β-chloroacrylaldehyde derivatives

A highly stereoselective synthesis of 1,6-dichloro-1,3,5-hexatriene derivatives by McMurry coupling of β-chloroacrylaldehydes have been developed.

A Novel Catalyst-Free Synthesis of 2,2-Diaryl Enamides from Stilbenes via a Nitrene Transfer Reaction

A novel catalyst-free nitrene transfer reaction between stilbenes and iminoiodinanes was achieved for the first time, which provides an efficient and environmentally friendly way to access variously substituted 2,2-diaryl enamides under mild conditions. Mechanistic investigations suggested the reaction proceed via nitrene transfer and aromatic rearrangement with iminoiodinane also acting as a Lewis acid, benefitting the ring-opening of the aziridine intermediate.

Facile utilisation of aldehyde bisulfite adducts: Synthesis of (E)-1,2- diphenylethenes

Background: A one-pot coupling reaction of aldehyde bisulfite adducts was developed for McMurry reaction using Zn-TiCl4 in 1,4-dioxane solvent medium. The treatment of sodium hydroxy(phenyl)methane sulfonate (2a) with TiCl4 in 1,4-dioxane favoured the deprotection of the bisulfite adduct 2a, and the in situ regeneration of benzaldehyde (1a) underwent reductive coupling to afford stilbene 3a in a relatively good yield, thus leading to an improved synthesis of a series of (E)-1,2- diphenylethenes 3. The present approach provides a new solution to the inherent instability of aldehydes and also provides a direct access to C'C bond formation for the synthesis of 1,2-diphenylethenes from aryl aldehyde bisulfite adducts. Methods: All reactions were performed at 70-80o and the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometric techniques. Results: The present approach provides a new solution to the instability of aldehydes and also provides a direct access to C'C bond formation for the synthesis of 1,2-diphenylethenes from aryl aldehyde bisulfite adducts. Conclusion: In the present work, we have reported an efficient method for the synthesis of 1,2- diphenylethene derivatives. Aldehydes are commonly used as the starting materials in the McMurry reaction, which affords the stilbene derivatives, the core skeleton of various valuable compounds. To increase the stability of the aldehydes, bisulfite adducts are usually employed, but the deprotection process causes loss of process efficiency. To address this issue, we developed a method based on the single-pot reaction of aromatic bisulfite adduct using TiCl4/Zn in 1,4-dioxane.

Copper-catalyzed double intramolecular ullmann coupling for the synthesis of diastereomerically and enantiomerically pure 4b,9b-dihydrobenzofuro[3,2-b]benzofurans

The copper-catalyzed double intramolecular Ullmann coupling of syn-1,2-bis(2-bromoaryl)ethane-1,2-diols with catalytic amounts of CuII oxinate as the copper source, K3PO4 as a base, and KI as a reductant in aqueous acetoni

Synthesis of 2-bromo-1-aryl-1H-indenes via a Ag(I) promoted domino 2π-electrocyclic ring-opening/4π-electrocyclization reaction of 1,2-diaryl substituted gem-dibromocyclopropanes

2-Bromo-1-aryl substituted indenes can be synthesized from 1,2-diaryl substituted gem-dibromocyclopropanes via a domino reaction sequence. The cascade reaction involves silver(I) promoted ionization and 2π-disrotatory electrocyclic ring-opening, followed by a 4π-conrotatory electrocyclic ring closing reaction of the allylic carbocation intermediate. Reaction conditions utilize silver tetrafluoroborate (AgBF4) in dichloroethane at 65 C. Selectivity effects for the electrocyclization were also studied. The 2-bromoindenes can be further functionalized using cross-coupling reactions, such as the Suzuki-Miyaura protocol. The alkene π-bond of the indenes can also be isomerized to give the thermodynamically more stable 2-bromo-3-aryl-1H-indene isomers using triethylamine in dichloromethane at room temperature.

Unequivocal experimental evidence for a unified lithium salt-free wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products

The true course of the lithium salt-free Wittig reaction has long been a contentious issue in organic chemistry. Herein we report an experimental effect that is common to the Wittig reactions of all of the three major phosphonium ylide classes (non-stabilized, semi-stabilized, and stabilized): there is consistently increased selectivity for cis-oxaphosphetane and its derived products (Z-alkene and erythro-β-hydroxyphosphonium salt) in reactions involving aldehydes bearing heteroatom substituents in the β-position. The effect operates with both benzaldehydes and aliphatic aldehydes and is shown not to operate in the absence of the heteroatom substituent on the aldehyde. The discovery of an effect that is common to reactions of all ylide types strongly argues for the operation of a common mechanism in all Li salt-free Wittig reactions. In addition, the results are shown to be most easily explained by the [2+2] cycloaddition mechanism proposed by Vedejs and co-workers as supplemented by Aggarwal, Harvey, and co-workers, thus providing strong confirmatory evidence in support of that mechanism. Notably, a cooperative effect of ortho-substituents in the case of semi-stabilized ylides is confirmed and is accommodated by the cycloaddition mechanism. The effect is also shown to operate in reactions of triphenylphosphine-derived ylides and has previously been observed for reactions under aqueous conditions, thus for the first time providing evidence that kinetic control is in operation in both of these cases.

Synthesis of stilbene analogues by one-pot oxidation-Wittig and oxidation-Wittig-Heck reaction

Synthesis of symmetrical (and unsymmetrical) stilbene derivatives is achieved by a combination of one-pot steps of Kornblum type oxidation of benzyl halide, its simultaneous in situ formation of phosphonium salt, and subsequently their Wittig reaction. In other variant it is oxidized to aldehyde, treated with ylide generated from phosphonium salt (CH3PPh3X) to give styrene, and subjected to Pd catalyzed Heck reaction with arylhalide to give stilbenes as the three-step one-pot sequence.

Convenient and stereoselective synthesis of symmetrical (E)-stilbenes via homocoupling of 1,3-dibenzylbenzotriazolium bromides

Using NaH as the base and DMSO as the solvent, a series of symmetric (E)-stilbenes were prepared in good yields via the -homocoupling of 1,3-dibenzylbenzotriazolium bromides at room temperature. Georg Thieme Verlag Stuttgart · New York.

Tandem pinacol coupling-rearrangement of aromatic aldehydes with hydrogen catalyzed by a combination of a platinum complex and a polyoxometalate

Together with a strongly oxidizing polyoxometalate, H5PV 2Mo10O40, PtII(N-(2,6- diisopropylphenyl)pyrazin-2-ylmethanimine)Cl2 forms a combined catalyst that was active in the tandem pinacol coupling-rearrangement of aryl aldehydes to give mostly the corresponding diarylacetaldehyde in high yields using molecular hydrogen as the reducing agent. The Royal Society of Chemistry.

Co-operative ortho-effects on the Wittig reaction. Interpretation of stereoselectivity in the reaction of ortho-halo-substituted benzaldehydes and benzylidenetriphenylphosphoranes

The E/Z ratios of the stilbenes 1 formed in the Wittig reaction of ortho-halo substituted benzyltriphenylphosphonium salts 2 and benzaldehydes 3 were determined. It was found that there is a co-operative effect of one ortho-halo group on each of the two reacting partners which increases Z-selectivity, but two such groups on the same reactant gives high E-selectivity. The effects are strong enough to be preparatively significant in certain cases and can be interpreted within the modern framework of the Wittig mechanism established by Vedejs and co-workers.