Silica triflate as an efficient reagent for the solvent-free synthesis of coumarins

Silica triflate,as a new silica-based reagent,can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions.All reactions were performed at 80℃in good to high yields.     

Highly efficient and easy synthesis of 2,4,6-triarylpyridines catalyzed by pentafluorophenylammonium triflate(PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions

Pentafluorophenylammonium triflate(PFPAT) was found to be a highly efficient catalyst for the preparation of 2,4,6- triarylpyridines from the reaction of acetophenone derivatives,aromatic aldehydes and ammonium acetate.Present methodology offers several advantages,such as short reaction time,high yields,simple procedure with an easy work-up and the absence of any volatile and hazardous organic solvent.In addition,this catalytic system can act as an active,inexpensive,metal-free,recoverable and recyclable catalyst.     

Pentafluorophenylammonium triflate as an efficient, environmentally friendly and novel organocatalyst for synthesis of bis-indolyl methane derivatives

A simple, inexpensive, environmentally friendly and efficient route for the synthesis of bis-indolyl methane derivatives by the reaction of indole or N-methyl indole with aldehydes using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. PFPAT organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.     

Vanadium(III) chloride as an effective catalyst for the Pechmann reaction

Good yields of substituted coumarins were obtained by a synthetic method involving the Pechmann reaction using vanadium(III)chloride (VCl₃) reagent to effect this condensation under solvent-free conditions. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 197–200, February, 2006.     

Anionic SO3H-functionalized ionic liquid: An efficient and recyclable catalyst for the Pechmann reaction of phenols with ethyl acetoacetate

This paper has reported an anionic SO₃H-functionalized ionic liquid N-methylimidazolium sulfomethylsulfonate ([Hmim][HO₃SCH₂SO₃]) for the synthesis of coumarins by Pechmann reaction. The [Hmim][HO₃SCH₂SO₃] is easier to prepare by one-step neutralization reaction of N-methylimidazole with methanedisulfonic acid and show high catalytic performance for Pechmann reaction. Besides, the catalyst can simply be separated from the reaction mixture and recycled ten times without noticeable loss of activity.     

Reductive coupling reaction of aldehydes using indium(III) triflate as the catalyst

A reductive coupling reaction was effectively developed to convert an aldehyde to its symmetrical ether. The successful reactions required Et₃SiH and CH₂Cl₂ as the suitable solvent in the presence of a catalytic amount of In(OTf)₃. Various aldehydes were subjected to the method, and each afforded the expected ethers in good to excellent yields.     

An efficient ZrCl4 catalyzed one-pot solvent free protocol for the synthesis of 4-substituted coumarins

A versatile and efficient route to 4-substituted coumarins via a Pechmann reaction using ZrCl₄ as the catalyst (10 mol %) is described. This method provides several advantages over alternative procedures such as mild, solvent-free conditions at ambient temperature, and direct isolation of the products in high yields.     

Microwave initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation

An energy-efficient protocol has been developed for solvent-free reactions that are mildly exothermic but not spontaneous. The exothermic reaction mixture—on several g-scale—is exposed for about 30 s to low power (about 200 W) microwaves and then the microwave oven is switched off. After this short burst of energy, the exothermic reaction gets initiated and proceeds on its own to completion. A number of coumarins were synthesized by the Pechmann reaction using this strategy.     

Pentafluorophenylammonium triflate: A highly efficient catalyst for the synthesis of quinoxaline derivatives in water

A simple, inexpensive, environmentally friendly and efficient route for the rapid and efficient synthesis of quinoxaline derivatives using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. Various quinoxaline derivatives were synthesized in good to excellent yields. The preparation of PFPAT catalyst from simple and readily available starting materials makes this method more affordable.     

Pentafluorophenylammonium triflate as a suitable and effective metal-free catalyst for the synthesis of quinazoline derivatives via one-pot multicomponent method

Research on Chemical Intermediates - A simple and facile synthesis of highly functionalized quinazoline derivatives has been successfully developed by treatment of aldehydes, ammonium acetate, and...     

A green and chemoselective synthesis of coumarins via Pechmann condensation using recoverable heterogeneous catalyst (Au@pSiO2)

Nano Au@porous SiO₂ as a heterogeneous catalyst was prepared and characterized by Fourier transform infrared, X-ray powder diffraction, transmission electron microscopy, thermogravimetric analysis and inductively coupled plasma–atomic emission spectroscopy techniques and then used as an efficient catalyst in the condensation of various phenols with ethyl acetoacetate for the preparation of coumarin derivatives through the Pechmann reaction. The combined merits of chemoselective and solvent free reaction conditions and the recyclability of the nanostructured catalyst make the condensation a safe operation, with low pollution, rapid access to products and simple workup.     

Use of a highly efficient and recyclable solid-phase catalyst based on nanocrystalline titania for the Pechmann condensation

Nanocrystalline titania-based sulfonic acid was used as an efficient and reusable catalyst for the synthesis of coumarins. The clean, mild acidity condition, the quantitative yields of products, the short reaction time, and the low reaction temperature are attractive features of this method, making it suitable for heat- or acid-sensitive substrates, particularly in drug synthesis. In practice, this method affords an advantageous combination of satisfactory yields, easy product isolation and purification.     

Ytterbium(III) triflate/TMSCI: efficient catalyst for imino ene reaction

[reaction: see text] Ytterbium trifluoromethanesulfonate [Yb(OTf)3] catalyzed the imino ene reaction of N-tosyl aldimine with alpha-methylstyrene to give a homoallylamine in moderate yield. Furthermore, addition of a catalytic amount of chlorotrimethylsilane (TMSCI) dramatically enhanced the imino ene reaction.     

Ceric Ammonium Nitrate (CAN): An Efficient Catalyst for the Coumarin Synthesis via Pechmann Condensation using Conventional Heating and Microwave Irradiation

An efficient and convenient method for the synthesis of substituted coumarins via Pechmann condensation of different phenols with ethylacetoacetate in the presence of ammonium cerium(IV) nitrate as the catalyst in a solvent- free media using both conventional heating and microwave irradiation.     

Sevelamer as an efficient and reusable heterogeneous catalyst for the Knoevenagel reaction in water

A catalyst system of Sevelamer, a phosphate-binding drug, has been prepared and used in the Knoevenagel reaction of aromatic aldehydes in water to produce substituted electrophilic alkenes. The products were obtained in excellent yields. Several novel, related catalytic systems showed promising catalytic properties for aromatic and heterocyclic aldehydes. The Sevelamer catalyst can be recovered using simple filtration and reused numerous times（up to 15 times） in the aqueous Knoevenagel reaction without any significant lowering of activity.     

Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepine derivatives

2,3-Dihydro-1H-1,5-benzodiazepines have been synthesized in solvent-free conditions in excellent yield from o-phenylenediamines and ketones in the presence of a catalytic amount of Sc(OTf)₃. This method is a very easy, rapid, and high yielding reaction for the synthesis of 1,5-benzodiazepine derivatives.     

Nanocrystalline TiO_2 as an efficient and reusable catalyst for the chemoselective trimethylsilylation of primary and secondary alcohols and phenols

Nanocrystalline TiO₂ was used as an efficient and recyclable catalyst for the chemoselective trimethylsilylation of primary and less hindered secondary alcohols and phenols with hexamethyldisilazane（HMDS）.All reactions were performed under mild and completely heterogeneous conditions in good to excellent yields.     

Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable zirconyl triflate, [ZrO(OTf)2]

In this paper, rapid and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane in the presence of catalytic amounts of ZrO(OTf)₂ is reported. Primary, secondary and tertiary alcohols as well as phenols were efficiently converted to their corresponding TMS ethers in short reaction times at room temperature. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols.     

Zinc oxide (ZnO) as a new, highly efficient, and reusable catalyst for acylation of alcohols, phenols and amines under solvent free conditions

Zinc oxide (ZnO) is a highly efficient catalyst for the acylation of a variety of alcohols, phenols and amines with acid chlorides or acid anhydrides under solvent free conditions. Primary, secondary, tertiary, allylic and benzylic alcohols, diols and phenols with electron donating or withdrawing substituents can be easily acylated in good to excellent yield.