4110-75-2

Upstream product

• 122-78-1 phenylacetaldehyde 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 68901-41-7 C₈H₇F₅Si^(2-)*2K⁽¹⁺⁾ 
• 124-41-4 sodium methylate 
• 108415-87-8 2-methoxy-2-phenyl-1-(phenylselenonyl)ethane 
• 108415-83-4 (E)-β-styryl phenyl selenone 
• 89036-92-0 C₁₅H₁₆O₃S 
• 536-74-3 phenylacetylene 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 14371-19-8 cis-β-methoxystyrene 
• 14371-25-6 2-bromo-1,1-dimethoxy-2-phenylethane 
• 38608-46-7 acetic acid-(α,β-dibromo-phenethyl ester) 
• 60466-40-2 (E)-phenyl(styryl)selane 

Downstream Products

• 96866-61-4 1α-phenyl-2β-methoxyoctahydroindolizine 
• 139632-90-9 5-Methyl-3,6,6-triphenyl-[1,2,4,5]trioxazinane 
• 122744-72-3 Dihydro-3,5,6,6-tetraphenyl-1,2,4,5-trioxazine 
• 622-42-4 1-nitro-1-phenylmethane 
• 100-52-7 benzaldehyde 
• 122744-70-1 trans-Dihydro-3,6-diphenyl-5-(phenylmethyl)-1,2,4,5-trioxazine 
• 150151-36-3 Dihydro-3,6-diheptyl-5-(phenylmethyl)-1,2,4,5-trioxazine 
• 122744-71-2 trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine 
• 263-06-9 6H,12H-Dibenzo<1,5>dithiocin 
• 110472-33-8 (2S,3R)-2-Methoxy-3-phenyl-thiochroman 
• 143064-65-7 (1R*,2S*,3R*)-3-(benzotriazol-1-yl)-1,2-diphenyl-1-ethoxy-3-methoxypropane 
• 106993-92-4 dimethoxy-1,1 phenyl-2 hexanone-5 
• 143064-64-6 (1R*,2S*,3R*)-3-(benzotriazol-1-yl)-1,2-diphenyl-1,3-dimethoxypropane 
• 110969-20-5 bromophenylacetaldehyde allyl ethyl acetal 

Relevant academic research and scientific papers

Synthesis of Non-Terminal Alkenyl Ethers, Alkenyl Sulfides, and N-Vinylazoles from Arylaldehydes or Diarylketones, DMSO and O, S, N-Nucleophiles

A transition-metal-free protocol for the synthesis of non-terminal alkenyl ethers, alkenyl sulfides, and N-vinylazoles from arylaldehydes or diarylketones, DMSO and O, S, N-nucleophiles has been reported. In this protocol, 24 examples of non-terminal alkenyl ethers and 28 examples of non-terminal alkenyl sulfides in 72–95% yields have been synthesized within 5 min. Moreover, 27 examples of non-terminal N-vinylazoles with 57–88% yields have also been synthesized within 2 hours. The preliminary mechanism investigations revealed that arylaldehydes or diarylketones offered a carbon atom, DMSO provided a methine and O, S, N-nucleophiles contributed one X atom for constructing C=C?X structure. (Figure presented.).

Variation on the π-Acceptor Ligand within a RhI?N-Heterocyclic Carbene Framework: Divergent Catalytic Outcomes for Phenylacetylene-Methanol Transformations

A series of neutral and cationic rhodium complexes bearing IPr {IPr=1,3-bis-(2,6-diisopropylphenyl)imidazolin-2-carbene} and π-acceptor ligands are reported. Cationic species [Rh(η4-cod)(IPr)(NCCH3)]+ and [Rh(CO)(IPr)(L)2]+ (L=pyridine, CH3CN) were obtained by chlorido abstraction in suitable complexes, whereas the cod-CO derivative [Rh(η4-cod)(IPr)(CO)]+ was formed by the carbonylation of [Rh(η4-cod)(IPr)(NCCH3)]+. Alternatively, neutral derivatives of type RhCl(IPr)(L)2 {L=tBuNC or P(OMe)3} can be accessed from [Rh(μ-Cl)(η2-coe)(IPr)]2. In addition, the mononuclear species Rh(CN)(η4-cod)(IPr) was prepared by cyanide-chlorido anion exchange, which after carbonylation afforded the unusual trinuclear compound [Rh{1κC,2κN-(CN)}(CO)(IPr)]3. Divergent catalytic outcomes in the phenylacetylene-methanol transformations have been observed. Thus, enol ethers, arisen from hydroalkoxylation of the alkyne, were obtained with neutral Rh?CO catalyst precursors whereas dienol ethers were formed with cationic catalysts. Variable amounts of alkyne dimerization, cyclotrimerization or polymerization products were obtained in the absence of a strong π-acceptor ligand on the catalyst.

MeOTf/KI-catalyzed efficient synthesis of 2-arylnaphthalenesviacyclodimerization of styrene oxides

The MeOTf/KI-catalyzed synthesis of 2-arylnaphthalene derivatives from aryl ethylene oxides in alcohol under ambient conditions is described. The present protocol has a higher atom efficiency and wider substrate applicability with excellent yields. The reaction proceeded using the aryl ethylene oxides to give 2-arylnaphthalenes either in homo-coupling or in cross-coupling. The reaction could also be carried out at the gram scale in minutes.

Base-promoted stereoselective hydroalkoxylation of alkynes

Base-promoted and stereoselective synthesis of C(sp2)-O bond through the anti-Markovnikov addition of alcohols onto alkyne and has been discovered. Developed protocol tolerates a wide variety of functional groups to afford styryl ethers from commercially

Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity

An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(5-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR

Z-selective, anti-Markovnikov addition of alkoxides to terminal alkynes: An electron transfer pathway?

Potassium alkoxides undergo anti-Markovnikov addition to aryl-substituted alkynes with Z selectivity in DMF as the solvent. The yields and efficiency of the reaction was also found to be enhanced by the addition of a secondary amine ligand such as N,N′-di

Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes

We report here the first transition-metal-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes to give enol ethers in high yields without using bases. Arylacetylenes as well as alkenyl- and alkylacetylenes were coupled with aliphatic alcohols, and the products were obtained with high Z selectivity in most cases. Effective catalysts were 8-quinolinolato rhodium complexes, which are structurally simple but have been relatively unexplored as catalysts.

Practical regioselective method for (E)-enol ehter

A new practical and highly regioselective synthetic method for (E)-enol ether is reported. (E)-enol ethers (E:Z = 93:7-99:1) were prepared from the corresponding enol acetates (E:Z?3:1) in two steps by bromination and anti- elimination of α-bromodialkylac

Solvolysis of styryliodonium salt: Products, rates, and mechanisms

The solvolysis of phenyl[(E)-styryl]iodonium tetrafluoroborate in various solvents was examined at 50-70°C by means of product and kinetic studies with the normal and labeled substrates. The reactions involved are α-elimination and substitutions with configurational retention and inversion. In methanol and ethanol, the main reaction is α-elimination, along with about 5% of substitution with the ratio of inversion/retention from 4/6 to 3/7. As the basicity of the solvent decreases, the reaction rate and the fraction of α-elimination decrease, and at the same time the ratio of inversion/retention of substitution also decreases. In 2,2,2- trifluoroethanol, only the substitution with retention was observed. Labeling experiments showed that complete isotope scrambling occurred between the olefinic hydrogens of the retained product while the deuterium remained at the original position of the inverted product. The substitution mechanism is concluded to involve parallel pathways: an S(N) 1-type with a vinylenebenzenium ion intermediate leading to retention and a vinylic S(N) 2- type with a direct attack by the nucleophilic solvent leading to inversion.

Cesium hydroxide catalyzed addition of alcohols and amine derivatives to alkynes and styrene

In the presence of catalytic amounts of cesium hydroxide (CsOH · H2O), alcohols, substituted anilines and heterocyclic amines undergo an addition in NMP to phenylacetylene leading to functionalized enol ethers and enamines. Anilines add to styrene (90-120°C, 12-14 h) leading to N-substituted anilines in satisfactory yields.