ZSM-5-SO3H as a novel, efficient, and reusable catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

Abstract  

ZSM-5 has been modified as supported sulfuric acid (ZSM-5-SO₃H) and introduced for the first time as a mild, convenient, reusable, and heterogeneous catalyst. Various types of aldehydes were efficiently converted to their 1,1-diacetates using a catalytic amount of ZSM-5-SO₃H in excellent yields under solvent-free and heterogeneous conditions at room temperature. The deprotection of 1,1-diacetates has also been achieved using this novel catalyst in ethanol. The procedure is operationally simple, environmentally benign, and only a stoichiometric amount of anhydride is used.     

PEG-SO3H as an efficient and reusable catalyst for chemoselective synthesis of 1,1-diacetates

An efficient and convenient procedure of the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature,in the presence of PEG-SO₃H is reported.PEG-SO₃H acts as a catalyst and can be recovered and reused eight times without apparent loss of its catalytic activity.     

Silica-bonded S-sulfonic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates

A simple and efficient procedure for the preparation of silica-bonded S-sulfonic acid (SBSSA) by reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in chloroform is described. This solid acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature.     

Polymer-supported gadolinium triflate as a convenient and efficient Lewis acid catalyst for acetylation of alcohols and phenols

A polymer-supported gadolinium triflate (CMPS-IM-Gd) catalyst was prepared from chloromethyl polystyrene (CMPS) resin using a simple and convenient procedure. This polymeric catalyst was used as an efficient Lewis acid catalyst for the acetylation of various alcohols and phenols with acetic anhydride, affording high yields under mild conditions. The reaction was completed in a short period of time with small amounts of the catalyst. The catalyst was reused over 10 times without any significant loss of its catalytic activity.     

Ferrous methanesulfonate as an efficient and recyclable catalyst for chemoselective synthesis of 1,1-diacetate from aldehydes

Ferrous methanesulfonate catalysing the conversion of aromatic,heteroaromatic,unsaturated,and aliphatic aldehydes to 1,1- diacetates at room temperature under solvent-free condition has been developed.The catalytic activity of seventeen metal methanesulfonates was compared under the same condition,ferrous methanesufonate proved to be the best.It can be easily recovered and reused for several times without distinct deterioration in catalytic activity.During the competitive protection between a ketone and ...     

P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions

An efficient and chemoselective method for the preparation of acylals from different aldehydes using P₂O₅/Al₂O₃ and acetic anhydride under solvent-free conditions.     

活性炭负载硫化锡纳米颗粒作为高效可重复使用Lewis酸催化剂催化三组分一锅法合成4H-吡喃[2,3-c]吡唑衍生物(英文)

Tin sulfide nanoparticles(SnS -NPs) were prepared in aqueous solution at room temperature on the surface of activated carbon(AC) and were investigated using field-emission scanning electron mi-croscopy(FE-SEM), transmission electron microscopy(TEM), X-ray diffraction, reflective ultravio-let-visible spectrophotometry, and spectrofluorimetry. Calculations based on the SEM and TEM images showed that the sizes of the SnS -NPs immobilized on the AC were 30–70 nm. The prepared nanocomposite was used as a heterogeneous Lewis acid catalyst for the three-components one-pot synthesis of 4H-pyrano[2,3-c]pyrazole derivatives in ethanol at 80 ℃. The reactions were efficiently performed in the presence of the prepared catalyst in short reaction times, and gave the desired products in high yields. This catalyst can be easily recovered by simple filtration and recycled up to eight consecutive times without significant loss of its efficiency.     

Tin sulfide nanoparticles supported on activated carbon as an efficient and reusable Lewis acid catalyst for three-component one-pot synthesis of 4H-pyrano[2,3-c]pyrazole derivatives

Tin sulfide nanoparticles (SnS‐NPs) were prepared in aqueous solution at room temperature on the surface of activated carbon (AC) and were investigated using field‐emission scanning electron mi‐croscop...     

聚乙烯基吡啶高氯酸盐作为高效固体酸催化剂在无溶剂条件下催化醛化学选择性制备二乙酸盐简

Poly(4-vinylpyridinium) perchlorate has been used as a supported, recyclable, environmentally-benign catalyst for the formation of acylals from aliphatic and aromatic aldehydes in good to excellent yields under solvent-free conditions. Notably, the reaction conditions were tolerant of ketones. This methodology offers several distinct advantages, including its operational simplicity and high product yield, as well as being green in terms of avoiding the use of toxic catalysts and solvents. Furthermore, the catalyst can be recovered and reused several times without any loss in its activity.     

Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H2O)

Aromatic and aliphatic aldehydes are transformed in 1,1-diacetates (acylals) in mild conditions, by a treatment with acetic anhydride and a Wells-Dawson acid (H₆P₂W₁₈O₆₂·24H₂O). gem-Diacetylation proceeds in Ac₂O with a little as 1% mol Wells-Dawson acid at room temperature and under solventless conditions, obtaining very good to excellent yields (88-98%) of 1,1-diacetates (19 examples). Neither 4-dimethylaminobenzaldehyde nor ketones react under the same conditions.     

TsOH-SiO2 as an efficient and eco-friendly catalyst for Knoevenagel condensation

Tosic acid on silica gel (TsOH-SiO₂) was synthesized and characterized using microscopic and spectroscopic techniques such as powder X-ray diffraction (XRD), scanning electron microscopy (SEM) and FT-IR spectroscopy. Thermal behaviour of the catalyst was investigated by differential scanning calorimetry (DSC) and thermogravimetric (TG) analysis. TsOH-SiO₂ showed excellent catalytic activity for the Knoevenagel condensation and was recyclable for six cycles.     

TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes

The combination of TiCl₃OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.     

An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions

The ability of titanium(IV) chloride as a catalyst to promote the Pechmann condensation reaction with a range of phenols and β-keto esters is described.The reaction was carried out by addition of TiCl₄ to a mixture of the phenol and the β-keto ester with thorough stirring in the absence of a solvent and represents an improvement on the classical Pechmann conditions. The yields of coumarins obtained via this novel protocol were significantly higher than those using the conventional method and the reaction duration was reduced to a few minutes or even a few seconds.     

Boric acid as an efficient catalyst for the synthesis of 1,1-diacetate under solvent-free condition

Boric acid (BO₃H₃) is an inexpensive, efficient and mild catalyst for the synthesis of 1,1-diacetate (acylal) from the various aromatic and heteroaryl aldehydes with acetic anhydride at room temperature under solvent-free condition. The present method does not involve any hazardous organic solvents or catalysts. This method gives notable advantages such as excellent chemoselectivity, mild reaction condition, short reaction times and excellent yield.     

Facile and green synthesis of triarylmethanes using silica sulfuric acid as a reusable catalyst under solvent-free conditions

A facile and environmentally-benign protocol has been developed for the synthesis of triarylmethanes (TAMs) from the reaction of different arenes and aldehydes in the presence of silica sulfuric acid (SSA) as a heterogeneous and reusable catalyst under solvent-free conditions. Easy work-up, short reaction times, high yields, high selectivity, mild and green conditions are other salient features of this method.     

Fe（HSO4）3： An efficient,heterogeneous and reusable catalyst for the synthesis of 14-aryl- or alkyl- 14H-dibenzo[a,j]xanthenes

Fe（HSO4）3 has been used as an efficient and recyclable catalyst for the one-pot synthesis of 14-aryl- or alkyl-14Hdibenzo[aj]xanthene derivatives by the reaction of 2-naphtol and aldehydes. Different types of aromatic and aliphatic aldehydes are used in the reaction and in all cases the products were obtained in good to excellent yields.     

KSF supported 10-molybdo-2-vanadophosphoric acid as an efficient and reusable catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazole derivatives under solvent-free condition

The one-pot three-component cyclocondensation has been developed involving the reaction of benzil with an aromatic aldehydes and ammonium acetate under thermal solvent-free conditions in the presence of a KSF supported 10-molybdo-2-vanadophosphoric acid catalyst. 10-Molybdo-2-vanadophosphoric acid was immobilized on KSF with a 20% loading, which showed the highest catalytic activity. The catalyst was fully characterized using FT-IR spectroscopy, thermal analysis, XRD and SEM analysis techniques. There are several distinct advantages to this protocol, including high yields, short reaction time, operational simplicity and a recyclable catalyst with a facile work-up procedure.     

Polystyrene resin-supported CuI-cryptand 22 complex: a highly efficient and reusable catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles under aerobic conditions in water

Polystyrene resin-supported copper(I) iodide-cryptand-22 complex (PS–C22–CuI) was synthesized and characterized by FT-IR, EDX, SEM, XPS, and TG-DTA analysis. This complex was found to be a highly active and robust heterogeneous catalyst for either three-component reaction of organic halides, sodium azide, and terminal alkynes, or the reaction of organic azides and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good to excellent yields at room temperature, using water as the green solvent. The catalyst can be not only easily isolated from the final product by filtration but also reused without significant loss of catalytic activity.