13343-79-8

Basic information

• Product Name: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis-
• CAS NO: 13343-79-8
• Molecular Formula: C16H12
• Molecular Weight: 204.271
• Mol File: 13343-79-8.mol
• Article Data: 285

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis-(13343-79-8)
• EPA Substance Registry System: Benzene, 1,1'-[(1E)-1-buten-3-yne-1,4-diyl]bis-(13343-79-8)

Safety Data

• Hazardous Substances Data: 13343-79-8(Hazardous Substances Data)

Upstream product

• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 103-64-0 bromostyrene 
• 6928-78-5 Bis(phenylethynyl)magnesium 
• 64-19-7 acetic acid 
• 536-74-3 phenylacetylene 
• 109-65-9 1-bromo-butane 
• 556-56-9 allyl iodid 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 4440-01-1 lithium phenylacetylide 
• 96-09-3 styrene oxide 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 90766-67-9 1-(4,4-dibromobuta-1,3-dien-1-yl)benzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 4666-89-1 2-Phenyl-3-trans-β-styryl-cyclopropenon 
• 1083-56-3 1,4-diphenylbutane 
• 538-81-8 1,4-diphenylbuta-1,3-diene 
• 62156-62-1 2,5-diphenyl-cyclopent-2-enone 
• 120999-45-3 (2E,3E)-2-benzylidene-4-phenylbut-3-enal 
• 116156-12-8 4-Phenyl-3-((E)-styryl)-5H-furan-2-one 
• 100-52-7 benzaldehyde 
• 3623-15-2 phenyl propargyl ketone 
• 143536-16-7 1,4-Diphenyl-but-3-yne-1,2-diol 
• 124475-79-2 2-(2-Phenyl-3-phenylethynyl-aziridin-1-yl)-isoindole-1,3-dione 
• 91-20-3 naphthalene 
• 612-94-2 2-phenylnaphthalene 
• 605-02-7 1-phenylnaphthalene 
• 13633-26-6 4-phenylbut-1-en-3-yne 

Relevant articles and documents

Kinetics and Mechanistic Insights into the Acetate-Assisted Dimerization of Terminal Alkynes under Ruthenium- and Acid-Promoted (RAP) Catalysis

The mechanism of the dimerization of terminal aryl alkynes promoted by [{RuCl(μ-Cl)(η6-p-cymene)}2](1)/AcOH, under cooperative transition metal/Br?nsted acid catalysis, has been investigated with regard to (i) the activation of the d

Pseudo-tetrahedral Rhodium and Iridium Complexes: Catalytic Synthesis of E-Enynes

The reactions of the rhodium(I) and iridium(I) complexes [M(PhBP3)(C2H4)(NCMe)] (PhBP3=PhB(CH2PPh2)3?) with alkynes have resulted in the synthesis of a new family of p

Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds

The efficient cross-coupling reactions of different alkynyl organozinc reagents with unsaturated organotellurium species catalyzed by Pd(PPh3)4/CuI and using THF/DMF systems are described. These cross-coupling reactions are general and permit the formation of new sp-sp2 carbon-carbon bonds. New reactions to reach the necessary alkynylzinc intermediates were also developed from terminal alkynes or using acetylenic tellurides as starting materials.

Influence of the gegenion in the transmetalation reaction of vinylic tellurides with higher order cyanocuprates

Dilithium cyanocuprates R2LCu(CN)Li2 (L=2-Th, Me) react with vinylic tellurides of Z configuration, RCH=CHTeR1 to give higher order vinylic cyanocuprates, [(RCH=CH)LCu(CN)Li2]. By changing the gegenion from lithium to magnesium [R2LCu(CN)LiMgBr or R2LCu(CN)(MgBr)2] the reaction gives cross - coupling products of Z configuration, RCH=CHR2 in good yields.

An unprecedented iridium(III) catalyst for stereoselective dimerisation of terminal alkynes

A novel iridium(III) hydride complex, IrHCl(TIMP3) (HTIMP 3, = tris[1 -(diphenylphosphino)-3-methyl-1 H-indol-2-yl]methane) was prepared and fully characterized in both the solid state and in solution. Chloride abstraction by silver

Terminal Alkyne Coupling Reactions through a Ring: Mechanistic Insights and Regiochemical Switching

The mechanism and selectivity of terminal alkyne coupling reactions promoted by rhodium(I) complexes of NHC-based CNC pincer ligands have been investigated. Synthetic and kinetic experiments support E- and gem-enyne formation through a common reaction seq

Can agostic interaction affect regiochemistry of carbopalladation? Reverse regioselectivity in the palladium-catalyzed dimerization of aryl acetylenes [22]

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Hydrocarboxylation of alkynes with formic acid over multifunctional ligand modified Pd-catalyst with co-catalytic effect

Hydrocarboxylation of terminal alkynes with formic acid (FA) was accomplished over a multifunctional ligand (L2) modified Pd-catalyst, advantageous with 100% atom-economy, free use of CO and H2O, mild reaction conditions, and high yields (56–89%) of α,β-unsaturated carboxylic acids with 100% regioselectivity to the branched ones. The multifunctional ligand of L2 as a zwitterion salt containing the phosphino-fragment (-PPh2), Lewis acidic phosphonium cation and sulfonate group (-SO3?), was constructed on the skeleton of 1.1′-binaphthyl-2.2′-diphenyl phosphine (BINAP) upon selective quaternization by 1,3-propanesultone. It was found that L2 conferred to the Pd-catalyst the co-catalytic effect, wherein the phosphino-coordinated Pd-complex was responsible for activation of all the substrates (including CO, FA and alkyne), and the incorporated phosphonium cation was responsible for synergetic activation of FA. The 1H NMR spectroscopic analysis supported that FA was truly activated by the incorporated Lewis acidic phosphonium cation in L2 via “acid-base pair” interaction. The in situ FT-IR spectra demonstrated that, the presence of Ac2O and NaOAc additives in the catalytic amount could dramatically promote the in situ release of CO from FA, which was required to initiate the hydrocarboxylation.

Stereo- A nd regioselective dimerization of alkynes to enynes by bimetallic syn-carbopalladation

Enynes are important motifs in bioactive compounds. They can be synthesized by alkynea'alkyne couplings for which a number of mechanisms have been suggested depending on catalyst type and dominant product isomers. Regarding bimetallic pathways, hydrometalations and anti-carbopalladations have been discussed to account for the formation of geminally substituted and (Z)-configured enynes, respectively. Here we report a bimetallic alkynea'alkyne coupling that yields (E)-configured enynes. An unusual type of acetylide Pd bridging was found in putative catalytic intermediates which is arguably responsible for the regio- A nd stereochemical reaction outcome. Mechanistic studies suggest that a double μa'κ:η2 acetylide bridging enables a bimetallic syn-carbometalation. Interestingly, depending on the reaction conditions, it is also possible to form the geminal regioisomer as major product with the same catalyst. This regiodivergent outcome is explained by bi-versus monometallic reaction pathways.

One-pot synthesis of α,β-unsaturated ketones through sequential alkyne dimerization/hydration reactions using the Hoveyda-Grubbs catalyst

Herein we report a sequential one-pot alkyne dimerization/hydration protocol for the regioselective synthesis of α,β-unsaturated ketones in quantitative yields. The alkyne dimerization reactions of terminal arylacetylenes proceeded with high regioselectivity in the presence of the Hoveyda-Grubbs 2nd generation catalyst (1 mol%) and tricyclohexylphosphine (4 mol%). The hydration reactions ofin situformed 1-aryl-3-en-1-ynes proceeded very rapidly in the presence of CCl3COOH/p-TsOH·H2O, yielding the corresponding unsaturated ketones within 15 minutes in quantitative yields. Different arylacetylene derivatives were converted to the corresponding α,β-unsaturated ketones in quantitative yields (94-95%) using sequential one-pot alkyne dimerization/hydration reactions.