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Relevant academic research and scientific papers

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.].

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

Sulfuric acid catalyzed addition of β-dicarbonyl compounds to alcohols under conventional heating and microwave-assisted conditions

The highly efficient direct addition of β-dicarbonyl compounds to secondary alcohols has been achieved using one of the cheapest acids, H 2SO4, as the catalyst. For a series of β-dicarbonyl compounds and various secondary alcohols, t

Highly efficient microwave-assisted substitution of β-dicarbonyl compounds with secondary alcohols using fluoroboric acid as the catalyst

The microwave-assisted substitution of β-dicarbonyl compounds with secondary alcohols has been achieved efficiently, using very cheap fluoroboric acid (HBF4) as the catalyst. For various β-dicarbonyl compounds and a series of secondary alcohols

Perchloric acid catalyzed homogeneous and heterogeneous addition of β-dicarbonyl compounds to alcohols and alkenes and investigation of the mechanism

(Figure presented) The direct addition of various β-dicarbonyl compounds to a series of secondary alcohols and alkenes has been achieved using 1 mol % perchloric acid (HClO4) as the catalyst. The HClO 4-catalyzed reactions could be conveniently conducted in commercial solvent and gave moderate to excellent yields. Moreover, the silica gel-supported HClO4 could also catalyze the heterogeneous addition for a series of substrates with similar or even higher yields in comparison with the homogeneous ones. The supported catalyst could be readily recovered and reused for four runs. Furthermore, the mechanism of the HClO4- catalyzed addition of the β-diketone to alcohol was investigated, and an SN1 mechanism was proved unambiguously for the first time through a series of experiments. The discrimination of catalytic abilities among different Bronsted acids was also rationalized by DFT calculations.

Amberlyst-15 in ionic liquid: an efficient and recyclable reagent for the benzylation and hydroalkylation of β-dicarbonyl compounds

Benzylation and hydroalkylation of 1,3-dicarbonyl compounds using Amberlyst-15 immobilized in ionic liquid [Bmim][PF6] as an efficient reusable reagent was studied. The reagent was compared with other solid acid reagents along with role of the ionic liquid. The effect of various reaction parameters like type of reagent, solvent, substrate molar ratio, reaction time, and temperature were studied. Present protocol is advantageous due to the ease in handling of reagent, simple work-up procedure, economical and environmentally benign process. The products were obtained in good to excellent yield and applicable to wide variety of substrates.

The lewis acidic ruthenium-complex-catalyzed addition of β-diketones to alcohols and styrenes is in fact brensted acid catalyzed

The Perchlorate salt of the dicationic bipy-ruthenium complex cis-[Ru(6,6′-Cl2bipy)2(H2O)2] 2+ effectively catalyzes addition of β-diketones to secondary alcohols and styrenes to yield the α-alkylated β-diketones. In a catalytic addition reaction of acetylacetone to 1-phenylethanol, the κ2-acetylacetonate complex [Ru(6,6′-Cl 2bipy)2(κ2-acac)]ClO4 was isolated after the catalysis; this complex is readily synthesized by reacting cis-[Ru(6,6′-Cl2bipy)2-(H2O) 2] (ClO4)2 with acetylacetone. [Ru(6,6′-Cl2bipy)2(κ-acac)]ClO4 is unreactive toward 1-phenylethanol in the presence of HClO4; it also fails to catalyze the addition of acetylacetone to 1-phenylethanol. On the basis of these observations, it is proposed and confirmed by independent experiments that the catalytic addition of β-diketones to the secondary alcohols is in fact catalyzed by the Bronsted acid HClO4, which is generated by the reaction of cis-[Ru(6,6′-Cl2bipy)2(H 2O)2]-(ClO4)2 with the β-diketone.