79341-79-0

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 67-56-1 methanol 
• 501-65-5 diphenyl acetylene 
• 451-40-1 phenyl benzyl ketone 
• 77-78-1 dimethyl sulfate 
• 591-50-4 iodobenzene 
• 4747-15-3 1-(2-methoxyvinyl)benzene 
• 108-86-1 bromobenzene 

Downstream Products

• 451-40-1 phenyl benzyl ketone 
• 93-58-3 benzoic acid methyl ester 
• 74145-94-1 2-(2-Hydroxy-phenyl)-2-methoxy-1-phenyl-ethanone 
• 1259437-13-2 2-fluoro-1,1-dimethoxy-1,2-diphenylethane 

Relevant academic research and scientific papers

ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis

Reported herein is an ortho-oxygenative 1,2-difunctionalization of diarylalkynes under merged gold/organophotoredox catalysis to access highly functionalized 2-(2-hydroxyaryl)-2-alkoxy-1-arylethan-1-ones. Detailed mechanistic studies suggested a relay process, initiating with gold-catalyzed hydroalkoxylation of alkynes, to generate enol-ether followed by a key formal [4+2]-cycloaddition reaction. The successful application of the present methodology was also shown for the synthesis of benzofurans.

A step forward in solvent knitting strategies: Ruthenium and gold phosphine complex polymerization results in effective heterogenized catalysts

Porous polymers based on ruthenium and gold triphenylphosphine complexes (KPhos(Ru), KPhos(Ru)Bi, KPhos(AuCl) and KPhos(AuNTf2)) were prepared via a cost-effective solvent knitting method with [RuHClCO(PPh3)3] or AuXPPh3 (X = Cl, NTf2) as single monomers or combined with biphenyl, which represents a further approach to obtain heterogenized catalysts. The resulting materials mainly preserve the metal coordination environment of their parent complexes, are stable up to 350 °C and have reasonable surface areas (250-300 m2 g-1 for KPhos(Ru)-polymers). KPhos(Ru)s selectively catalyze the imination of alcohols in the presence of base and the results for KPhos(Au)s show they are effective for the intermolecular hydration and hydroamination of alkynes. These materials can be reused several times without significant loss of activity. This novel and simple method affords heterogenized catalysts that combine the reactivity and selectivity of their homogeneous counterparts with the stability and reusability of a heterogeneous framework.

Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading

The use of [(IPr)AuOH] as versatile, air- and moisture-stable pre-catalyst permits the in situ generation of the cationic gold(I) species [(IPr)Au]X after reaction with a Br?nsted acid. This catalytic system presents as a main advantage the lack of use of a silver salt activator or co-catalyst which is often air-, light- and moisture-sensitive. A general gold(I)-catalyzed procedure using this in situ activation at very low catalyst loading is reported for the hydration of a broad range of internal and terminal alkynes.

Isolable gold(I) complexes having one low-coordinating ligand as catalysts for the selective hydration of substituted alkynes at room temperature without acidic promoters

Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)-phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones in nearly quantitative yields. Acid-labile groups present in the substrates are preserved. The catalytic activity strongly depends on both the nature of the phosphine coordinated to the gold (I) center and the softness of the counteranion, the complex AuSPhOsNTf2 showing the better activity. A plausible mechanism for the hydration of alkynes through ketal intermediates is proposed on the basis of kinetic studies. The described catalytic system should provide an efficient alternative to mercury-based methodologies and be useful in synthetic programs.

Heck reactions of 2-substituted enol ethers with aryl bromides catalysed by a tetraphosphine/palladium complex

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of β-substituted enol ethers with aryl bromides. Employing β-methoxystyrene, 3-ethoxyacrylonitrile or methyl 3-methoxyacrylate, the regioselective α-arylation of these enol ethers was observed in all cases, and mixtures of Z and E isomers were generally obtained, which in many cases yielded a single ketone product after acid treatment. The stereoselectivity of this reaction depends on steric and electronic factors, and better stereoselectivities in favour of Z isomers were observed with electron-rich or sterically congested aryl bromides. Better yields were obtained for this reaction with electron-rich or sterically congested aryl bromides than with electron-poor aryl bromides. This observation suggests that with these β-substituted enol ethers the rate-limiting step of the catalytic cycle is not the oxidative addition of the aryl bromide to the palladium complex.

Titanium-Mediated Carbonyl Olefinations. 2. Benzylidenations of Carbonyl Compounds with Dibenzyltitanocene

Mild thermolysis of carbonyl compounds with dibenzyltitanocene affords phenyl-substituted olefins, enol ethers, and enamines.

THE BEHAVIOUR OF DISUBSTITUTED ALKYNES WITH VARIOUS METAL ION ACETATES

4-Octyne and diphenylethyne have been treated with some metal ion acetates in methanol and in acetic acid.From this systematic investigation, it appeares that the metal ions play a major role in directing the course of the reaction.The function of the metal is not predictable, since no general trend has been observed.Mercuric acetate was by and large the best reagent for the reaction with alkynes, quantitatively transforming these substrates into vinyl ethers, ketones, and dimethylketals.The reaction was faster in methanol than in acetic acid, and 4-octyne resulted more reactive than diphenylethyne.

HYDROXIDE ION INITIATED REACTIONS UNDER PHASE TRANSFER CATALYSIS CONDITIONS II. THE ROLES OF WATER AND QUAT

The effects of water molecules and quat structure are shown to be significant in determining the behavior of alkylation reactions of weakly acidic carbon acids under PTC/OH(1-) conditions.