5186-08-3

Upstream product

• 585-71-7 (1-bromoethyl)benzne 
• 123-54-6 acetylacetone 
• 5185-90-0 C₁₃H₁₅ClHgO₂ 
• 14024-48-7 bis(acetylacetonato)cobalt(II) 
• 672-65-1 (1-chloroethyl)benzene 
• 4335-90-4 3-benzylidene acetylacetone 
• 1445-79-0 trimethyl gallium 
• 100-42-5 styrene 
• 98-85-1 1-Phenylethanol 
• 93-96-9 bis(1-phenylethyl)ether 
• 100-41-4 ethylbenzene 
• 4809-56-7 N-(1-phenylethyl)-p-toluenesulfonamide 

Downstream Products

• 1140821-53-9 3-(1-phenylethyl)-4-(trimethylsilyloxy)pent-3-en-2-one 
• 2848-25-1 2-acetoxyphenol 
• 17913-10-9 1-methyl-3-phenyl-butanal 
• 782-02-5 4-(α-Methylbenzyl)-1,2-dihydroxybenzene 
• 77473-29-1 1,2-dimethoxy-4-(1-phenylethyl)benzene 
• 5831-65-2 1-(2-methyl-4-phenyl-4,5-dihydrofuran-3-yl)ethanone 
• 1046126-93-5 1-phenyl-1-(2,4,6-trimethoxyphenyl)ethane 

Relevant academic research and scientific papers

Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound

Monoallylation and monoalkylation of diketones and β-keto esters with allylic and benzylic alcohols catalysed by [Cp*Co(CH3CN)3][SbF6]2(I) are reported. The method does not require any additive and affords regioselective products. The mechanistic investigations were done byin situ1H NMR spectroscopy as well as control experiments. It has been shown that reactions proceedviaη3-allyl complex formation or ally ether intermediate. The alkylation takes placeviaonly ether intermediate. The resulting allylated and alkylated products have been used for the synthesis of eleven new trisubstituted pyrazoles and one pyrazolone.

Graphene oxide catalyzed ketone α-alkylation with alkenes: Enhancement of graphene oxide activity by hydrogen bonding

Direct α-alkylation of carbonyl compounds represents a fundamental bond forming transformation in organic synthesis. We report the first ketone-alkylation using olefins and alcohols as simple alkylating agents catalyzed by graphene oxide. Extensive studies of the graphene surface suggest a pathway involving dual activation of both coupling partners. Notably, we show that polar functional groups have a stabilizing effect on the GO surface, which results in a net enhancement of the catalytic activity. The method represents the first alkylation of carbonyl compounds using graphenes, which opens the door for the development of an array of protocols for ketone functionalization employing common carbonyl building blocks and readily available graphenes.

Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach

Abstract: Sulfamic acid stabilized on the surface of silica by the n-propyl organic group linker which is named silica-bonded N-propylsulfamic acid was applied as an efficient heterogeneous catalyst with good recyclability and reusability for direct benzylation of 1,3-dicarbonyl compounds using secondary aromatic alcohols or styrenes as alkylating agents in high yields and short reaction times. All the reactions were carried out in nitromethane as solvent under an air atmosphere. The catalyst showed reusable feature by six times without a significant loss in its activity. Graphical abstract: [Figure not available: see fulltext.].

Solvent-free alkylation of 1,3-dicarbonyl compounds with benzylic, propargylic and allylic alcohols catalyzed by La(NO3)3·6H2O

An efficient and solvent free method for benzylation, propargylation and allylation of 1,3-dicarbonyl compounds with alcohols has been developed by using La(NO3)3·6H2O as water tolerable catalyst. The reaction was shown to proceed smoothly for various 1,3-dicarbonyl compounds with benzylic, propargylic and allylic alcohols including 1° allylic alcohols, without any solvent, providing a clean access to the desired products in short reaction times with good to excellent yields and high selectivity.

Synthesis and structure of an air-stable bis(isopropylcyclopentadienyl) zirconium perfluorooctanesulfonate and its catalyzed benzylation of 1,3-dicarbonyl derivatives with alcohols

An air-stable uninuclear complex of bis(isopropylcyclopentadienyl) zirconium perfluorooctane sulfonate (1a·H2O·3THF) was successfully synthesized by the reaction of (i-PrCp)2ZrCl2 with C17SO3Ag. The c

Carbon-supported iron-ionic liquid: An efficient and recyclable catalyst for benzylation of 1,3-dicarbonyl compounds with alcohols

The effect of the addition of ILs with non-coordinating anions on the iron-catalyzed benzylation of 1,3-dicarbonyl compounds with alcohols under solvent free conditions has been evaluated. Among them, the presence of those containing the bistriflimide anion was found to be crucial for selectivity towards the benzylated product in a homogenous reaction. Therefore, the catalytic activity of Fe(OTf)3-N4111NTf2 combination supported on carbon materials with different textural and chemical surface properties has been studied. In the heterogeneous phase, reaction selectivity was also enhanced by the addition of the IL. However, substantial differences between the activities of different Fe-IL/carbon material catalytic systems were observed, indicating the influence of carbon support properties. With regards to selectivity, the best results were obtained using carbon supports with low microporosity. Moreover, the presence of oxygen functional groups on the carbon surface improved catalyst recycling. the Partner Organisations 2014.

Fe(HSO4)3 : An efficient, heterogeneous and reusable catalyst for C-alkylation of β-dicarbonyl compounds

Fe(HSO4)3(FHS) was used as an efficient catalyst for the heterogeneous addition of a series of benzylic and allylic alcohols to various β-dicarbonyl compounds, which afforded moderate to excellent yields of C-alkylated products in 1,2-dichloroethane. In comparison with the previous methods, the present research surprisingly exhibited higher reaction yields without formation of any by-products which could be formed by self-condensation of alcohols. Moreover, the catalyst can be readily recovered and reused up to five times with almost maintained reactivity and yields.

The efficiency of the metal catalysts in the nucleophilic substitution of alcohols is dependent on the nucleophile and not on the electrophile

In this study, we investigate the effect of the electrophiles and the nucleophiles for eight catalysts in the catalytic SN1 type substitution of alcohols with different degree of activation by sulfur-, carbon-, oxygen-, and nitrogen-centered nucleophiles. The catalysts do not show any general variance in efficiency or selectivity with respect to the alcohols and follow the trend of alcohol reactivity. However, when it comes to the nucleophile, the eight catalysts show general and specific variances in the efficiency and selectivity to perform the desired substitution. Interestingly, the selectivity of the alcohols to produce the desired substitution products was found to be independent of the electrophilicity of the generated carbocations but highly dependent on the ease of formation of the cation. Catalysts based on iron(III), bismuth(III), and gold(III) show higher conversions for S-, C-, and N-centered nucleophiles, and BiIII was the most efficient catalyst in all combinations. Catalysts based on rhenium(I) or rhenium(VII), palladium(II), and lanthanum(III) were the most efficient in performing the nucleophilic substitution on the various alcohols with the O-centered nucleophiles. These catalysts generate the symmetrical ether as a by-product from the reactions of S-, C-, and N-centered nucleophiles as well, resulting in lower chemoselectivity. Who's the boss? In a comprehensive study of catalytic S N1 type direct substitution of alcohols, the catalysts do not show any general variance in efficiency or selectivity with respect to the alcohols but are highly variable with respect to the nucleophiles. The reactivity of the alcohols is independent of the electrophilicity of the generated carbocations but highly dependent on the ease of formation of the cation.

Ruthenium salophen triflate: A reusable catalyst for alkylation of 1,3-dicarbonyl compounds

Reaction of 1,3-dicarbonyl compounds with alcohols or olefins in the presence of catalytic amounts of electron-deficient [Ru(salophen)OTf] produced α-alkylated 1,3-dicarbonyls under solvent-free conditions. Different substituted benzylic alcohols were efficiently reacted with 2,4-pentanedione or 1,3-diphenyl-1,3-propanedione and their corresponding alkylated diones were obtained in good to excellent yield. On the other hand, substituted styrenes were also converted to their corresponding α-alkylated 1,3-dicarbonyls in good yields. The effect of reaction parameters such as solvent, amount of catalyst and axial substituent on the ruthenium salophen was also investigated. The catalyst was reusable several times without loss of its activity.

Different products in the reaction of the alcohols with cyclic and acyclic 1,3-dicarbonyl compounds: K5CoW12O40 as an electron transfer nano catalyst

K5CoW12O40 was used as a highly effective catalyst for the benzylation of 1,3-dicarbonyl compounds. β-Keto enol ethers were obtained when cyclic 1,3-dicarbonyl compounds used in this conditions instead of linear ones. The present methodology offers a practical, simple, mild, environmentally friendly, and time-saving method for etherification. Very low loading of catalyst, ease of workup, ease of handling, and reusability of catalyst are other advantages of this catalyst.